US3565804A - Lubricating oil additives - Google Patents

Lubricating oil additives Download PDF

Info

Publication number
US3565804A
US3565804A US23959A US3565804DA US3565804A US 3565804 A US3565804 A US 3565804A US 23959 A US23959 A US 23959A US 3565804D A US3565804D A US 3565804DA US 3565804 A US3565804 A US 3565804A
Authority
US
United States
Prior art keywords
hydrocarbon
molecular weight
carbon atoms
alkylene
percent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US23959A
Inventor
Lewis R Honnen
Robert Gordon Anderson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Application granted granted Critical
Publication of US3565804A publication Critical patent/US3565804A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/58Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/18Introducing halogen atoms or halogen-containing groups
    • C08F8/20Halogenation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/30Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/238Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/54Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06Well-defined aromatic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024Propene
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06Perfluorinated compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02Esters of silicic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • C10N2040/26Two-strokes or two-cycle engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Definitions

  • Hydrocarbon polyamines having a long, substantially aliphatic, oil solubilizing hydrocarbon chain bonded to a dior higher polyamine which find use as detergents and dispersants in both lubricating oils and in fuels.
  • the hydrocarbon group is normally branched and derived from natural sources or polyolefins,
  • the compounds of this invention are long chain hydrocarbon substituted polyamines, the amino groups being bonded to aliphatic carbon atoms.
  • the hydrocarbon group is an oil solubilizing group relatively free of aromatic unsaturation.
  • the additives of this invention do not themselves contribute significantly to the formation of sludge and deposits, They are able to stably disperse depositforming materials in the oil medium, while avoiding any significant enhancement of the rate of formation of deposit-forming materials by their own degradation products.
  • Patents of interest include the following.
  • US. Pat. No. 3,182,024 is concerned with a N-amino alkyl or polyamino polyalkylene long chain hydrocarbon substituted pyrrolidine which finds use as a detergent in lubricating oil.
  • U.S. Pats. Nos. 3,031,505 and 3,189,652 are concerned with hydrocarbon substituted alkylene polyamines, primarily propane diamines and amine compounds up to C These compounds are used as reactants to be reacted with glycidyl halides followed by reaction with alkylene polyamines.
  • the final product finds use in maintaining sediment-forming materials dispersed in fuels, The only exemplification are C straight chain aliphatic substituted propane diamines.
  • Long branched chain, primarily aliphatic, hydrocarbon substituted polyamines are provided of from about 600 to 10,000 average molecular weight which are efiective detergents in lubricating oils and fuels.
  • the hydrocarbon group will normally be derived from mineral oils of high molecular weight or polyolefins by halogenation of the hydrocarbon and displacement of the halogen with an appropriate polyamine, normally free of unsaturation.
  • compositions of this invention are high molecular weight branched chain aliphatic hydrocarbon N-substituted alkylene polyamines which are superior detergents and dispersants in both lubricating oils and hydrocarbonaceous fuels for internal combustion engines, being effective under wide variations in operating conditions.
  • the compositions have average molecular weights in the range of about 600 to 10,000, more usually in the range of about 750 to 5,000. With the lower molecular weight hydrocarbon groups, the average number of groups will be greater than one.
  • the hydrocarbon groups will normally be aliphatic, having from 0 to 2 sites of unsaturation, more usually from 0 to 2 sites of ethylenic unsaturation and preferably from 0 to 1 site of ethylenic unsaturation.
  • the hydrocarbon group will normally be derived from a polyolefin derived from olefins of from 2 to 6 carbon atoms (ethylene being copolymerized with an olefin of at least 3 carbon atoms), or from a high molecular weight petroleum-derived hydrocarbon.
  • compositions of this invention will have the following formula:
  • U is alkylene of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms, there being at least 2 carbon atoms between the nitrogen atoms;
  • a is an integer of from 0 to 10, usually of from 1 to 6,
  • b is an integer of from 0 to 1 and preferably 0;
  • a+2b is an integer of from 1 to 10, more usually an integer of from 1 to 6 and preferably an integer of from 1 to 4;
  • c is an integer or fractional number (when averaged over the entire composition) in the range of from 1 to 5, preferably 1 to 3, and equal to or less than the number of nitrogen atoms in the molecule, usually on the average less than the total number of nitrogen atoms in the molecule;
  • R is an aliphatic or alicyclic branched chain hydrocarbon radical derived from petroleum hydrocarbons or olefin monomers of from 2 to 6 carbon atoms, preferably of from 3 to 4 carbon atoms, ethylene being copolymerized with a higher homologue (an olefin of at least 3 carbon atoms) and having from 0 to 2 sites of ali phatic unsaturation, more usually from 0 to 2 sites of ethylenic unsaturation and preferably from 0 to 1 site of ethylenic unsaturation having greater than 40 carbon atoms and not more than 300 carbon atoms, more usually 50 to 200 carbon atoms and preferably 60 to 200 carbon atoms.
  • the alkylene radical indicated as U, will have from 2 to 6 carbon atoms, the nitrogens connected by U being separated by at least 2 carbon atoms.
  • the alkylene group may be straight chain or branched chain, the remaining valences of the alkylene group being on different carbon atoms.
  • Illustrative alkylene groups include ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, 1,2-propylene, 2-methy1-l,3-propylene, l,4-(2,3-dimethylbutylene), etc.
  • the hydrocarbon radical indicated by R may be aliphatic or alicyclic and, except for adventitious amounts of aromatic structure present in petroleum mineral oils, will be free of aromatic unsaturation.
  • the hydrocarbon groups are derived from petroleum mineral oil or polyolefins, either homo-polymers or higher order polymers, of l-olefins of from 2 to 6 carbon atoms, ethylene being polymerized with a higher homologue.
  • the olefins may be monoor polyunsaturated, but the polyunsaturated olefins require that the final product be reduced to remove substantially all of the residual unsaturation.
  • Illustrative sources for the high molecular weight hydrocarbons from petroleum mineral oils are naphthenic bright stocks.
  • illustrative polymers include polypropylene, polyisobutylene, poly-l-butene, copolymer of ethylene and isobutylene, copolymer of propylene and isob-utylene, poly-l-pentene, poly-4-methyl-1- pentene, poly-l-hexene, poly-3-methylbutene-l, etc.
  • the hydrocarbon group will normally have at least 1 branch per 6 carbon atoms along the chain, preferably at least 1 branch per 4 carbon atoms along the chain, and particularly preferred that there be from 0.5 to 1 branch per carbon atom along the chain (at least 1 branch per 2 carbon atoms along the chain).
  • These branched chain hydrocarbon groups are readily prepared by the polymerization of olefins of from 3 to 6 carbon atoms and preferably from olefins of from 3 to 4 carbon atoms.
  • the addition polymerizable olefins employed are normally l-olefins.
  • the branch will be of from 1 to 4 carbon atoms, more usually of from 1 to 2 carbon atoms and preferably methyl.
  • the generic formula does not indicate to which nitrogen atom the R group and the H atoms are bonded. Rather, free valences are indicated by bars, and the total number of R groups and H atoms indicated next to the basic polyamine structure.
  • the generic formula employed provides a simple means for including the possible variations that will occur when a polyamine is used having nonequivalent amine nitrogen atoms.
  • R is a polyisobutenyl group.
  • the composition is a mixture of materials having varying structures and molecular weights. Therefore, in referring to molecular weight, viscosity average molecular weights are intended. Furthermore, when speaking of the particular hydrocarbon group, it is intended that the group include the mixture that is normally contained with materials which are commercially available; that is, polyisobutylene is known to have a range of molecular weights and may also include very small amounts of very high molecular weight materials. Furthermore, depending on the method of preparation, the end group of the polymer may vary and may be terminated, not only with an isobutene group, but also with a 1- or Z-butene group.
  • alkylene polyamines which are commercially available are frequently mixtures of various alkylene polyamines having one or two species dominating.
  • tetraethylene pentamine there will also be small amounts of pentaethylene hexamine and triethylene tetramine.
  • tetraethylene pentamine for example, it is intended not only to include the pure compound, but those mixtures which are obtained with commercially available alkylene polyamines.
  • the product will be a mixture of the various possible isomers.
  • alkylene polyamines may have only one hydrocarbon substituent or may be polysubstituted with hydrocarbon radicals.
  • the monosubstituted alkylene polyarnine compositions will have the following formula:
  • N-polyisobutenyl ethylene diamine N-polypropenyl ethylene diamine, N poly(1 butenyl) ethylene diamine, N-(alternating copolymer of ethylene and isobutylene) ethylene diamine (alternating copolymers of ethylene and isobutylene may be achieved by the cationic polymerization of 4 methylpentene l), N-polypropenyl 2 aminoethylpiperazine, N polyisobutenyl 2 aminoethylpiperazine, N polypropenyl diethylene triamine, N- polyisobutenyl diethylene triamine, N poly(l-pentenyl) diethylene triamine, N polypropenyl trimethylene diamine, N polyisobutenyl trimethylene diamine, N polypropenyl di(trimethylene) triamine, N polyisobutenyl di(trimethylene) triamine, N-polyisobutenyl
  • the polyhydrocarbon radical substituted alkylene polyarnine compositions have the following formula:
  • U, a, b and R are as defined previously and d is a fractional or whole number greater than 1 and up to 5, more usually from about 1.2 to 4 and preferably from about 1.5 to 4, averaging over the entire composition.
  • the number of hydrocarbon substituents need not be a whole number when averaging over the total composition; generally, a mixture will be obtained containing mono-, di-, and trior higher substituted molecules averaging out to a fractional or whole number.
  • the hydrocarbon groups may be the same or different, differing both as to molecular weight and structure. Normally, the hydrocarbon groups will be primarily the same structure and differ only as to molecular weight.
  • the shorter hydrocarbon chains ranging toward the lower end of the molecular weight range to have on the average more than one hydrocarbon group, particularly as the number of amine nitrogens per molecule increases.
  • N,N'-di(polypropenyl) diethylene triamine N,N (polyisobutenyl) diethylene triamine, N,N' di(polyisobutenyl) triethylene tetramine
  • N,N' di (polypropenyl) tetraethylene pentamine N,N' di(polyisobutenyl) tetraethylene pentamine
  • N,N,N" tri(polyisobutenyl) tetraethylene pentamine
  • N,N' di(polyisobutenyl) 2 aminoethylpiperazine N,N' di(poly 1- butenyl) triethylene tetramine, N,N di(polyisobutenyl) di- (trimethylene) triamine, etc.
  • compositions of this invention will have the following formula:
  • U is alkylene of from 2 to 3 carbon atoms (ethylene or propylene) and preferably ethylene;
  • a is an integer of from 1 to 5, more usually of from 1 c is an integer of from 1 to 5, more usually of from 1 to 3 and (on the average) equal to or less than the number of nitrogen atoms;
  • R is a branched chain aliphatic hydrocarbon group having from 0 to 2 sites of olefinic unsaturation derived from olefins of from 2 to 6 carbon atoms (ethylene is copolymerized with an olefin of at least 3 carbon atoms) and preferably derived from olefins of from 3 to 4 atoms, being either a homopolymer or higher order polymer (co-, ter-, etc.) and having a molecular weight in the range of about 600 to 2800, more usually of from about 750 to about 2000.
  • the preferred R groups are polypropylene, polyisobutylene or combinations thereof.
  • the alkenylene polyarnine When 0 is equal to one, the alkenylene polyarnine will be mono-substituted. When 0 is greater than 1, usually averaging over the entire composition in the range of about 1.25 to 3, the alkylene polyarnine will normally be a mixture of monoand higher order substitution.
  • alkylene polyamines are the ethylene polyamines having from 2 to 6 amino nitrogen groups. When these are substituted with a branch chain aliphatic hydrocarbon group, these compositions will have the following formula:
  • a is an integer of from 1 to 5, more usually from 1 to 4;
  • c is an integer or fractional number of from 1 to 4, more usually of from 1 to 3 and preferably being in the range of about 1 to 2;
  • R is a branched chain aliphatic hydrocarbon group derived from polymerizing olefins of from 3 to 4 carbon atoms and having a molecular weight in the range of about 650 to 2800, more usually 750 to 2000.
  • Preferred R s are polypropenyl, polyisobutenyl or combinations thereof, either mixtures or copolymers.
  • compositions of this invention are readily prepared by combining an aliphatic or alicyclic halide with the desired amine in the proper mole proportions.
  • the halide is prepared from the hydrocarbon by halogenation: ionically or free radically.
  • the hydrocarbon groups may be prepared by ionic or free radical polymerization of olefins of from 2 to 6 carbon atoms (ethylene must be copolymerized with another olefin) to an olefin of the desired molecular weight.
  • the olefins which find use are ethylene, propylene, isobutylene, l-butene, l-pentene, 3--methyl-1- pentene, 4 methyl-l-pentene, etc., preferably propylene and isobutylene.
  • the preferred olefins, propylene and isobutylene have from 0.5 to 1 branch per atom along the hydrocarbon chain.
  • various naturally occurring materials may be used which have the desiredmolecular weight and aliphatic or alicyclic character.
  • the halogen may be introduced into the hydrocarbon molecule by various means known in the art. Most readily, either chlorine or bromine (halogen of atomic number 17-35) may be introduced by the free radical catalyzed halogenation of the hydrocarbon, or ionic addition to olefinic unsaturation.
  • Various free radical catalysts may be used, such as peroxides, azo compounds, bromine, iodine, as well as light. Ionic catalysts are exemplified by ferric chloride. Methods of halogenation are well known in the art and do not require extensive exemplification or illustration here.
  • the amount of halogen introduced will depend on the particular hydrocarbon used, the desired amount of amine to be introduced into the molecule, the particular alkylene amine used, and the halogen used.
  • the amount of halogen introduced will generally be in the range from about 1 to 5 halogen atoms per molecule, depending on the reactivity of the resulting halide. On a weight percent basis, the amount of halide will generally range from about 1 to 25, more usually from about 1 to 10.
  • the halohydrocarbon and alklylene polyamine or polyalkylene polyamine may be brought together neat or in the presence of an inert solvent, particularly a hydrocarbon solvent.
  • the inert hydrocarbon solvent may be aliphatic or aromatic.
  • aliphatic alcohols may be used by themselves or in combination with another solvent, when capable of dissolving the reactants.
  • the reaction may be carried out at room temperature C.), but elevated temperatures are preferred. Usually, the temperature will be in the range of from about 100 to 225 C. Depending on the temperature of the reaction, the particular halogen used, the mole ratios and the particular amine, as well as the reactant concentrations, the time may vary from 1 to 24 hours, more usually from about 3 to 20 hours. Times greatly in excess of 24 hours do not particularly enhance the yield and may lead to undesirable degradation. It is therefore preferred to limit the reaction time to fewer than 24 hours.
  • the mole ratio of halohydrocarbon to alkylene amine will generally be in the range from about 0.2 to 10 moles of alkylene amine per mole of halohydrocarbon, more usually 0.5 to 5 moles of alkylene amine per mole of halohydrocarbon.
  • the mole ratio will depend upon the amount of halogen present in the halohydrocarbon, the particular halogen and the desired ratio of hydrocarbon to amine. If complete suppression of polysubstitution of the alkylene polyamines is desired, then large mole excesses of the amine will be used.
  • the residual halogen as bound halogen will be in the range of 0 to 10 weight percent of the composition.
  • Small amounts of halogen may be present as the hydrohalide salt of the hydrocarbon substituted alkylene polyamines.
  • the hydrocarbons used will have aliphatic unsaturation.
  • the amines may react in a way resulting in the elimination of hydrogen halide, introducing further aliphatic unsaturation into the hydrocarbon radical. Therefore, the hydrocarbon radicals usually will be olefinically unsaturated.
  • the olefinic unsaturation does not significantly affect the utility of the product, and when available, saturated aliphatic halide may be used.
  • the reaction mixture may be extracted with a hydrocarbon medium to free the product from any low molecular weight amine salt which has formed.
  • the product may then be isolated by evaporation of the solvent. Further separation from unreacted hydrocarbon or purification may be carried out as desired, e.g., chromatography.
  • the reaction may be carried out in the medium in which it will ultimately find use and be formed at concentrations which provide a concentrate of the detergent composition.
  • the final reaction mixture may be in a form to be used directly upon dilution in lubricating oils or fuels.
  • Example A Into a reaction flask was introduced 950 g. of polyisobutylene (approximate molecular weight:950) dissolved in 1,000 ml. of carbon tetrachloride. The mixture was 8 stirred and chlorine was introduced at a rate of 235-250 ml. per minute, the temperature being maintained at 0 C. After the reaction mixture had taken up 51 g. of chlorine, the introduction of chlorine was terminated, the carbon tetrachloride removed in vacuo and the chlorinated polyisobutylene isolated.
  • Example 3 Into a reaction flask was introduced 1,780 g. of brominated polyisobutylene (polyisobutylene of approximately 930 average molecular weight brominated to 8.6 weight percent bromine) and 350 g. of a mixture of polyethylene amines having an average composition of tetraethylene pentamine and allowed to stand overnight at ambient temperatures. The mixture was then heated at 150 C. for several hours (approximately 5 to 6), cooled and diluted with several volumes of n-pentane and allowed to stand. The solution was then concentrated to about one-half its original volume, about 1 liter of ethanol and about 1 liter of 10 percent aqueous sodium carbonate added.
  • brominated polyisobutylene polyisobutylene of approximately 930 average molecular weight brominated to 8.6 weight percent bromine
  • a mixture of polyethylene amines having an average composition of tetraethylene pentamine and allowed to stand overnight at ambient temperatures.
  • the mixture was then heated at 150 C.
  • Example 4 Into a reaction flask was introduced 433 g. of chlorinated polyisobutylene (polyisobutylene of approximately 950 average molecular weight chlorinated to 9.3 weight percent chlorine) and 240 g. of alkylene polyamine having an average composition of tetraethylene pentamine and 640 ml. of benzene added. The mixture was heated to reflux and the benzene distilled off. The residue was then heated at 150 C. for 4 hours. After cooling the reaction mixture and diluting with mixed hexanes, 200 ml.
  • chlorinated polyisobutylene polyisobutylene of approximately 950 average molecular weight chlorinated to 9.3 weight percent chlorine
  • alkylene polyamine having an average composition of tetraethylene pentamine and 640 ml. of benzene
  • Example 6 Into a reaction flask was introduced 3,000 g. of a 70 weight percent solution in benzene of chloropolyisobutylene (polyisobutylene of approximately 1,300 molecular weight chlorinated to 4.3 weight percent chlorine) and 210 g. of alkylene polyamine having an average composition of triethylene tetramine and the mixture heated to reflux, the benzene stripped off and the mixture further heated at 170 C. for 4 hours. At the end of this time, the mixture was allowed to cool, and then diluted with equal volumes of mixed hexanes and absolute ethanol, heated to reflux and then one-third volume of weight percent aqueous sodium carbonate added.
  • chloropolyisobutylene polyisobutylene of approximately 1,300 molecular weight chlorinated to 4.3 weight percent chlorine
  • alkylene polyamine having an average composition of triethylene tetramine
  • Example 8 Into a reaction flask was introduced 800 g. of benzene, 846 g. of chlorinated polyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight percent) and 300 g. of alkylene polyamine having an average composition of triethylene tetramine and the mixture heated to reflux and benzene gradually stripped oil. The temperature was then increased to 175 C. and maintained for 3.5 hours. After allowing the mixture to cool, equal volumes of both mixed hex-anes and 95 percent ethanol were added and the resulting solution separated into 2 equal portions. One of the portions was allowed to sit in a separatory funnel and the alcoholic phase permitted to separate.
  • chlorinated polyisobutylene polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight percent
  • alkylene polyamine having an average composition of triethylene tetramine
  • chloropolyisobutylene polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight
  • compositions of this invention find a wide variety of uses under a wide variety of conditions.
  • the subject compositions find use as detergents and dispersants in lubricating oils for internal combustion engines, automobile engines, in two-cycle engines, as well as in fuels for internal combustion engines, particularly gasoline engines.
  • UTILITY Preferred compositions which find use in lubricating oils, both for the automobile and the diesel engines, will for the most part have the following formula:
  • U is alkylene of from 2 to 3 carbon atoms, preferably ethylene
  • a is an integer of from 1 to 5, more usually from 2 to 4;
  • c is an integer or fractional number in the range of from 1 to 3, more usually in the range of 1 to 2, and equal to or less than the number of amine nitrogen atoms,
  • R is a branched chain aliphatic hydrocarbon radical derived by polymerization of olefins of from 3 to 4 carbon atoms and of from about 700 to 3,000 molecular weight, more usually from about 750 to 2,800 average molecular weight.
  • the preferred R groups are polypropylene and polyisobutylene.
  • the detergents may be prepared as concentrates having as high as 80 weight percent of the detergent in lubricating oil. Generally, concentrates will vary from about to 80 weight percent. However, when the oil is to be used in the engine, the amount of the detergent generally will vary from about 0.1 to weight percent, more usually from 0.25 to 10 Weight percent. The lubricating oil compositions may therefore vary in the amount of detergent from 0.1 to 80 weight percent.
  • compositions of this invention can be used with various base oils which find use as lubricating oils.
  • Naturally occurring base oils include naphthenic base, parafiin base, asphaltic base and mixed base lubricating oils.
  • Synthetic hydrocarbon oils include alkylene polymers, such as polymers of propylene, butylene, l-octene, and mixtures thereof and alkylated aromatic hydrocarbons.
  • Nonhydrocarbon lubricating oils include: alkylene oxide type polymers; carboxylic acid esters such as octyl adipate, nonyl azelate, decyl suberate, butyl alkenylsuccinate, etc.; also, inorganic esters such as phosphates and silicates.
  • the above base oils may be used individually or in combination, whenever miscible or made so by the use of mutual solvents.
  • the detergents of this invention are used in lubricating oils with an oxidation inhibitor and extreme pressure agent.
  • the preferred inhibitors are metal dithiophosphates, particularly zinc 0,0-di(hydrocarbyl) phosphorodithioate, where the hydrocarbyl groups are generally from 4 to 36 carbon atoms.
  • Hydrocarbyl is an organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof, e.g., aralkyl or alkaryl, and may be aliphatically saturated or unsaturated, e.g., ethylenic unsaturation.
  • the hydrocarbyl groups are alkyl or alkaryl groups.
  • S-alkyl and S-polyalkyleneoxy esters of the phosphorodithioate may be used. Usually, about 6 to 50 mM./kg. of the phosphorodithioate is used in the oil.
  • additives may also be included in the lubricating oil. These additives include pour point depressants, viscosity index improvers, antiwear agents, rust inhibitors, corrosion inhibitors, other detergents and dispersants, etc. Generally, the total amount of additives exclusive of the detergent will be in the range of from about 0.1 to 5 weight percent of the lubricating oil composition.
  • a special situation in which the detergents of this invention are employed in lubricating oils are lubricating oils for two-cycle engines.
  • the oil is incorporated with the fuel and burned directly in the piston chamber.
  • compositions for use in the two-cycle engine oil have the following formula:
  • U is alkylene of from 2 to 3 carbon atoms, preferably ethylene
  • a is an integer of from 1 to 4, preferably 2 to 4;
  • 0 is an integer or fractional number of from 1 to 2
  • R is a branched chain aliphatic hydrocarbon radical derived from a polyolefin obtained from olefins of from 3 to 4 carbon atoms and having a molecular weight in the range of about 650 to 3,000, more usually from about 750 to 2,000.
  • the preferred polymers are polypropylene and polyisobutylene.
  • hydrocarbonaceous lubricating oils will be used, particularly petroleum derived, such as the mixed base, parafiinic and naphthenic base oils.
  • hydrocarbonaceous lubricating oils will be used, particularly petroleum derived, such as the mixed base, parafiinic and naphthenic base oils.
  • phosphorodithioate inhibitors other oxidative inhibitors such as bis(phenols), etc. may be used.
  • concentrations in the oil may be as low as one mM./kg.
  • a halide scavenger for the lead may also be added, usually to enhance the halide already present in the gasoline.
  • Alkylene halide scavengers such as ethylene dibromide may be used with the detergent compositions of this invention, but aryl halides, e.g., dichlorobenzene, are preferred.
  • aryl halides e.g., dichlorobenzene
  • Other additives already described for the lubricating oils, may also be included.
  • the first test was the L-l Supp. 1 (MIL-L-2l04B, Supp. 1 Specifications).
  • the oil was formulated containing 0.03 weight percent nitrogen and 8 mM./kg. of 0,0- dialkyl phosphorodithioate (alkyl of from 4 to 6 carbon atoms) in a Mid-Continent SAE 30 base oil.
  • the test was carried out for 120 hours, the following table indicating the results.
  • the Yamaha engine test uses a 75 cc. Model YG-1 motorcycle engine. The same conditions as described for the McCulloch engine are also used for the Hyundai engine.
  • compositions of this invention having a wide variety of structures and a wide variation in hydrocarbon to amine nitrogen ratio, provide effective detergency and dispersancy under a great variety of conditions. Not only are they eflective in the lubricating oils of the automobile engine and in the much hotter conditions in the diesel engine, but they are also effective in two-cycle engines as well.
  • the engine is a Model 1-81 approximately 85 cc. displacement. The test is carried out for 10 hours, the engine being run at 7,000 r.p.m., at a temperature of 435 F. and with a wide open throttle. Using regular gasoline, a fuel-oil mixture in the ratio of 20:1 is prepared, the oil composition being a blend of detergent in SAE 40 grade base oil, such that wherein:
  • U is alkylene of from 2 to 6 carbon atoms
  • a is an integer of from 0 to 10;
  • b is an integer of from 0 to 1;
  • (1+2! is an integer of from 1 to 10;
  • c is an integer or fractional number in the range of 1 to 5, and equal to or less than the number of nitrogen atoms in the molecule;
  • R is of from 40 to 300 carbon atoms and is an aliphatic or alicyclic branched chain hydrocarbon radical derived from petroleum hydrocanbons or polyolefins of monomers from 2 to 6 carbon atoms, with the proviso that when the monomer is ethylene, it is copolymerized with a higher homologue.
  • composition according to claim 1 wherein:
  • a is of from 1 to 6;
  • a+2b is of from lto 6;
  • 15 c is of from 1 to 3; and R is a polyolefin of from 50 to 200 carbon atoms.
  • composition according to claim 1 wherein: b is and R is a polyolefin derived from olefins of from 3 to 4 carbon atoms. 4.
  • U is alkylene of from 2 to 3 carbon atoms
  • a is an integer of from 1 to 5;
  • c is an integer of from 1 to 5 and, on the average, equal to or less than the number of nitrogen atoms;
  • R is of from about 600 to 2,800 average molecular weight and is a branched chain aliphatic hydrocarbon polyolefin derived from olefins of from 2 to 6 carbon atoms, with that proviso that when the monomer is ethylene, it is copolymerized with a higher homologue. 5.
  • a is of from 1 to 4;
  • c is of from 1 to 3;
  • R is a polyolefin derived from olefins of from 3 to 4 carbon atoms, and of about 600 to 2,800 average molecular weight. 6. A composition according to claim 5, wherein R is of from about 750m about 2,000 molecular weight.
  • composition according to claim 4 wherein c is one.
  • composition according to claim 4 wherein c is in the range of about 1.25 to 3.
  • a is in the range of 1 to 5;
  • c is in the range of 1 to 4 and equal to or less than the number of nitrogen atoms
  • R is a branched chain aliphatic hydrocarbon group derived from olefins of from 3 to 4 carbon atoms and of an average molecular weight in the range of about 650 to 2,800. 10.
  • a is in the range of 1 to 4.
  • c is in the range of 1 to 2;
  • R is polypropenyl or polyisobutenyl of from about 750 to 2,000'molecular weight. 11.
  • a lubricating oil composition having from 0.1 to weight percent of a composition according to claim 1 and an oil of lubricating viscosity.
  • a lubricating oil composition having from 10 to 80 weight percent of a composition according to claim 1 and an oil of lubricating viscosity.
  • a lubricating oil composition having from 0.1 to 80 weight percent of a composition according to claim 4 and an oil of lubricating viscosity.
  • a lubricating oil composition having from 0.1 to 80 weight percent of a composition according to claim 9 and an oil of lubricating viscosity.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

HYDROCARBON POLYAMINES ARE PROVIDED HAVING A LONG, SUBSTANTIALLY ALIPHATIC, OIL SOLUBILIZING HYDROCARBON CHAIN BONDED TO A DI- OR HIGHER POLYAMINE WHICH FIND USE AS DETERGENTS AND DISPERSANTS IN BOTH LUBRICATING OILS AND IN FUELS. THE HYDROCARBON GROUP IS NORMALLY BRANCHED AND DERIVED FROM NATURAL SOURCES OR POLYOLEFINS.

Description

United States Patent 3,565,804 LUBRICATING OIL ADDITIVES Lewis R. Honnen, Petaluma, Calif., and Robert Gordon Anderson, Wassenaar, Netherlands, assignors to Chevron Research Company, San Francisco, Calif., a corporation of Delaware No Drawing. Continuation-impart of applications Ser. No. 408,686, Nov. 3, 1964, and Ser. No. 488,775, Sept. 20, 1965. This application Mar. 30, 1970, Ser. No. 23,959
Int. Cl. C07c 87/04; (107d 51/70; C10m 1/32 US. Cl. 25250 23 Claims ABSTRACT OF THE DISCLOSURE Hydrocarbon polyamines are provided having a long, substantially aliphatic, oil solubilizing hydrocarbon chain bonded to a dior higher polyamine which find use as detergents and dispersants in both lubricating oils and in fuels. The hydrocarbon group is normally branched and derived from natural sources or polyolefins,
CROSS-REFERENCES TO RELATED APPLICA- TIONS This application is a continuation-in-part of application Ser. No. 488,775, filed Sept. 20, 1965, and Ser. No. 408,686, filed Nov. 3, 1964.
BACKGROUND OF THE INVENTION Field of the invention The compounds of this invention are long chain hydrocarbon substituted polyamines, the amino groups being bonded to aliphatic carbon atoms. The hydrocarbon group is an oil solubilizing group relatively free of aromatic unsaturation.
These compounds are effective detergents and dispersants in both lubricating oils and fuels for internal combustion engines. In internal combustion engines, the presence of constricted openings and narrow tolerances in the areas of moving parts provides numerous opportunities for deposits to seriously reduce the operating efiiciency of the engines. The lubricating oil must be capable of maintaining sludge forming deposits dispersed in the oil, thus keeping the piston and piston rings relatively free of deposits. Also, sludge formation is minimized in the crankcase and in the areas where valves and gears operate.
In addition, the additives of this invention do not themselves contribute significantly to the formation of sludge and deposits, They are able to stably disperse depositforming materials in the oil medium, while avoiding any significant enhancement of the rate of formation of deposit-forming materials by their own degradation products.
Description of the prior art Patents of interest include the following. US. Pat. No. 3,182,024 is concerned with a N-amino alkyl or polyamino polyalkylene long chain hydrocarbon substituted pyrrolidine which finds use as a detergent in lubricating oil.
U.S. Pats. Nos. 3,031,505 and 3,189,652 are concerned with hydrocarbon substituted alkylene polyamines, primarily propane diamines and amine compounds up to C These compounds are used as reactants to be reacted with glycidyl halides followed by reaction with alkylene polyamines. The final product finds use in maintaining sediment-forming materials dispersed in fuels, The only exemplification are C straight chain aliphatic substituted propane diamines.
U.S. Pats. Nos. 2,267,204, 2,267,205, 2,361,457 and 2,891,850 are all concerned with low molecular weight polyamines.
SUMMARY OF THE INVENTION Long branched chain, primarily aliphatic, hydrocarbon substituted polyamines are provided of from about 600 to 10,000 average molecular weight which are efiective detergents in lubricating oils and fuels. The hydrocarbon group will normally be derived from mineral oils of high molecular weight or polyolefins by halogenation of the hydrocarbon and displacement of the halogen with an appropriate polyamine, normally free of unsaturation.
DETAILED DESCRIPTION OF THE INVENTION The compositions of this invention are high molecular weight branched chain aliphatic hydrocarbon N-substituted alkylene polyamines which are superior detergents and dispersants in both lubricating oils and hydrocarbonaceous fuels for internal combustion engines, being effective under wide variations in operating conditions. The compositions have average molecular weights in the range of about 600 to 10,000, more usually in the range of about 750 to 5,000. With the lower molecular weight hydrocarbon groups, the average number of groups will be greater than one. The hydrocarbon groups will normally be aliphatic, having from 0 to 2 sites of unsaturation, more usually from 0 to 2 sites of ethylenic unsaturation and preferably from 0 to 1 site of ethylenic unsaturation.
The hydrocarbon group will normally be derived from a polyolefin derived from olefins of from 2 to 6 carbon atoms (ethylene being copolymerized with an olefin of at least 3 carbon atoms), or from a high molecular weight petroleum-derived hydrocarbon.
For the most part, the compositions of this invention will have the following formula:
wherein:
U is alkylene of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms, there being at least 2 carbon atoms between the nitrogen atoms;
a is an integer of from 0 to 10, usually of from 1 to 6,
and more usually of from 1 to 4;
b is an integer of from 0 to 1 and preferably 0;
a+2b is an integer of from 1 to 10, more usually an integer of from 1 to 6 and preferably an integer of from 1 to 4;
c is an integer or fractional number (when averaged over the entire composition) in the range of from 1 to 5, preferably 1 to 3, and equal to or less than the number of nitrogen atoms in the molecule, usually on the average less than the total number of nitrogen atoms in the molecule; and
R is an aliphatic or alicyclic branched chain hydrocarbon radical derived from petroleum hydrocarbons or olefin monomers of from 2 to 6 carbon atoms, preferably of from 3 to 4 carbon atoms, ethylene being copolymerized with a higher homologue (an olefin of at least 3 carbon atoms) and having from 0 to 2 sites of ali phatic unsaturation, more usually from 0 to 2 sites of ethylenic unsaturation and preferably from 0 to 1 site of ethylenic unsaturation having greater than 40 carbon atoms and not more than 300 carbon atoms, more usually 50 to 200 carbon atoms and preferably 60 to 200 carbon atoms.
The alkylene radical, indicated as U, will have from 2 to 6 carbon atoms, the nitrogens connected by U being separated by at least 2 carbon atoms. The alkylene group may be straight chain or branched chain, the remaining valences of the alkylene group being on different carbon atoms. Illustrative alkylene groups include ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, 1,2-propylene, 2-methy1-l,3-propylene, l,4-(2,3-dimethylbutylene), etc.
The hydrocarbon radical indicated by R may be aliphatic or alicyclic and, except for adventitious amounts of aromatic structure present in petroleum mineral oils, will be free of aromatic unsaturation. The hydrocarbon groups are derived from petroleum mineral oil or polyolefins, either homo-polymers or higher order polymers, of l-olefins of from 2 to 6 carbon atoms, ethylene being polymerized with a higher homologue. The olefins may be monoor polyunsaturated, but the polyunsaturated olefins require that the final product be reduced to remove substantially all of the residual unsaturation.
Illustrative sources for the high molecular weight hydrocarbons from petroleum mineral oils are naphthenic bright stocks. For the polyolefin, illustrative polymers include polypropylene, polyisobutylene, poly-l-butene, copolymer of ethylene and isobutylene, copolymer of propylene and isob-utylene, poly-l-pentene, poly-4-methyl-1- pentene, poly-l-hexene, poly-3-methylbutene-l, etc.
The hydrocarbon group will normally have at least 1 branch per 6 carbon atoms along the chain, preferably at least 1 branch per 4 carbon atoms along the chain, and particularly preferred that there be from 0.5 to 1 branch per carbon atom along the chain (at least 1 branch per 2 carbon atoms along the chain). These branched chain hydrocarbon groups are readily prepared by the polymerization of olefins of from 3 to 6 carbon atoms and preferably from olefins of from 3 to 4 carbon atoms. The addition polymerizable olefins employed are normally l-olefins. The branch will be of from 1 to 4 carbon atoms, more usually of from 1 to 2 carbon atoms and preferably methyl.
The above formula provides for alkylene polyamines and alkylene amines and polyamines attached to a piperazine ring. Therefore, when a and b are both 1 the formulae would be as follows:
NR2 H2 CHZNH CH1 CHzN with RX, where the R group will replace from one to two of the hydrogen atoms, a complex product would be obtained. There are three different nitrogen atoms which may react to form a mono-substituted product. The three isomers are:
(CHM
RNI'I CH2 CH NH CH2 CH N NH R 11202 NIIgCHzCHzllICHzCHzN NH and NHzGHzCHzNHOHzOHzN The disubstituted product would add three more compounds.
'In order to include all possible variations, the generic formula does not indicate to which nitrogen atom the R group and the H atoms are bonded. Rather, free valences are indicated by bars, and the total number of R groups and H atoms indicated next to the basic polyamine structure. The generic formula employed provides a simple means for including the possible variations that will occur when a polyamine is used having nonequivalent amine nitrogen atoms.
Looking at Example 1, infra, where a monopolyisobutenyl tetraethylene pentamine is prepared, for that compound, the generic formula:
would have a equal to 4, b equal to 0, 0 equal to l, U would be ethylene, and R would be a polyisobutenyl group of approximately 930 average molecular weight. The three possible mono (polyisobutenyl) tetraethylene pentamines would have the following formulae:
It is possible to prepare single compounds. With monopolyisobutenyl ethylene diamine, only one isomer can be formed:
where R is a polyisobutenyl group. With higher order polyamines, while it is possible to form a single isomer, as a practical matter, this will rarely be done.
In preparing the compositions of this invention, rarely will a single compound be employed. With both the polymers and the petroleum-derived hydrocarbon groups, the composition is a mixture of materials having varying structures and molecular weights. Therefore, in referring to molecular weight, viscosity average molecular weights are intended. Furthermore, when speaking of the particular hydrocarbon group, it is intended that the group include the mixture that is normally contained with materials which are commercially available; that is, polyisobutylene is known to have a range of molecular weights and may also include very small amounts of very high molecular weight materials. Furthermore, depending on the method of preparation, the end group of the polymer may vary and may be terminated, not only with an isobutene group, but also with a 1- or Z-butene group.
In addition the alkylene polyamines which are commercially available are frequently mixtures of various alkylene polyamines having one or two species dominating. Thus, in commercially available tetraethylene pentamine, there will also be small amounts of pentaethylene hexamine and triethylene tetramine. In referring to tetraethylene pentamine, for example, it is intended not only to include the pure compound, but those mixtures which are obtained with commercially available alkylene polyamines. Finally, as indicated, in preparing the compounds of this invention, where the various nitrogen atoms of the alkylene polyamine are not equivalent, the product will be a mixture of the various possible isomers.
As is evident from the above formula, the alkylene polyamines may have only one hydrocarbon substituent or may be polysubstituted with hydrocarbon radicals. The monosubstituted alkylene polyarnine compositions will have the following formula:
wherein U, a, b and R have been previously defined.
Illustrative compounds within the above formula are as follows: N-polyisobutenyl ethylene diamine, N-polypropenyl ethylene diamine, N poly(1 butenyl) ethylene diamine, N-(alternating copolymer of ethylene and isobutylene) ethylene diamine (alternating copolymers of ethylene and isobutylene may be achieved by the cationic polymerization of 4 methylpentene l), N-polypropenyl 2 aminoethylpiperazine, N polyisobutenyl 2 aminoethylpiperazine, N polypropenyl diethylene triamine, N- polyisobutenyl diethylene triamine, N poly(l-pentenyl) diethylene triamine, N polypropenyl trimethylene diamine, N polyisobutenyl trimethylene diamine, N polypropenyl di(trimethylene) triamine, N polyisobutenyl di(trimethylene) triamine, N-polyisobutenyl 1,2 propylene diamine, N polyisobutenyl di(1,2 propylene) triamine, N polypropenyl triethylene tetramine, N polyisobutenyl triethylene tetramine, N (alternating copolymer of ethylene and isobutylene) triethylene tetramine, N polypropenyl tetraethylene pentamine, N polyisobutenyl tetraethylene pentamine, N-polyiso butenyl pentaethylene hexamine, etc.
The polyhydrocarbon radical substituted alkylene polyarnine compositions have the following formula:
wherein U, a, b and R are as defined previously and d is a fractional or whole number greater than 1 and up to 5, more usually from about 1.2 to 4 and preferably from about 1.5 to 4, averaging over the entire composition.
(As indicated by the above formula, the number of hydrocarbon substituents need not be a whole number when averaging over the total composition; generally, a mixture will be obtained containing mono-, di-, and trior higher substituted molecules averaging out to a fractional or whole number.) The hydrocarbon groups may be the same or different, differing both as to molecular weight and structure. Normally, the hydrocarbon groups will be primarily the same structure and differ only as to molecular weight.
It is preferred with the shorter hydrocarbon chains ranging toward the lower end of the molecular weight range to have on the average more than one hydrocarbon group, particularly as the number of amine nitrogens per molecule increases.
Illustrative compounds coming within the above formula are as follows: N,N'-di(polypropenyl) diethylene triamine, N,N (polyisobutenyl) diethylene triamine, N,N' di(polyisobutenyl) triethylene tetramine, N,N' di (polypropenyl) tetraethylene pentamine, N,N' di(polyisobutenyl) tetraethylene pentamine, N,N,N" tri(polyisobutenyl) tetraethylene pentamine, N,N' di(polyisobutenyl) 2 aminoethylpiperazine, N,N' di(poly 1- butenyl) triethylene tetramine, N,N di(polyisobutenyl) di- (trimethylene) triamine, etc.
Usually, the compositions of this invention will have the following formula:
U is alkylene of from 2 to 3 carbon atoms (ethylene or propylene) and preferably ethylene;
a is an integer of from 1 to 5, more usually of from 1 c is an integer of from 1 to 5, more usually of from 1 to 3 and (on the average) equal to or less than the number of nitrogen atoms; and
R is a branched chain aliphatic hydrocarbon group having from 0 to 2 sites of olefinic unsaturation derived from olefins of from 2 to 6 carbon atoms (ethylene is copolymerized with an olefin of at least 3 carbon atoms) and preferably derived from olefins of from 3 to 4 atoms, being either a homopolymer or higher order polymer (co-, ter-, etc.) and having a molecular weight in the range of about 600 to 2800, more usually of from about 750 to about 2000. The preferred R groups are polypropylene, polyisobutylene or combinations thereof.
When 0 is equal to one, the alkenylene polyarnine will be mono-substituted. When 0 is greater than 1, usually averaging over the entire composition in the range of about 1.25 to 3, the alkylene polyarnine will normally be a mixture of monoand higher order substitution.
Commonly available alkylene polyamines are the ethylene polyamines having from 2 to 6 amino nitrogen groups. When these are substituted with a branch chain aliphatic hydrocarbon group, these compositions will have the following formula:
a is an integer of from 1 to 5, more usually from 1 to 4;
c is an integer or fractional number of from 1 to 4, more usually of from 1 to 3 and preferably being in the range of about 1 to 2; and
R is a branched chain aliphatic hydrocarbon group derived from polymerizing olefins of from 3 to 4 carbon atoms and having a molecular weight in the range of about 650 to 2800, more usually 750 to 2000. Preferred R s are polypropenyl, polyisobutenyl or combinations thereof, either mixtures or copolymers.
METHOD OF PREPARATION The compositions of this invention are readily prepared by combining an aliphatic or alicyclic halide with the desired amine in the proper mole proportions. The halide is prepared from the hydrocarbon by halogenation: ionically or free radically.
As already indicated, the hydrocarbon groups may be prepared by ionic or free radical polymerization of olefins of from 2 to 6 carbon atoms (ethylene must be copolymerized with another olefin) to an olefin of the desired molecular weight. The olefins which find use are ethylene, propylene, isobutylene, l-butene, l-pentene, 3--methyl-1- pentene, 4 methyl-l-pentene, etc., preferably propylene and isobutylene.
As previously indicated, there should be at least 1 propylene, isobutylene, l-butene, l-pentene, 3-methyl-lbranch per 4 carbons along the chain and preferably at least 1 branch per 4 carbons along the chain. The preferred olefins, propylene and isobutylene, have from 0.5 to 1 branch per atom along the hydrocarbon chain.
Alternatively, various naturally occurring materials may be used which have the desiredmolecular weight and aliphatic or alicyclic character.
The halogen may be introduced into the hydrocarbon molecule by various means known in the art. Most readily, either chlorine or bromine (halogen of atomic number 17-35) may be introduced by the free radical catalyzed halogenation of the hydrocarbon, or ionic addition to olefinic unsaturation. Various free radical catalysts may be used, such as peroxides, azo compounds, bromine, iodine, as well as light. Ionic catalysts are exemplified by ferric chloride. Methods of halogenation are well known in the art and do not require extensive exemplification or illustration here.
The amount of halogen introduced will depend on the particular hydrocarbon used, the desired amount of amine to be introduced into the molecule, the particular alkylene amine used, and the halogen used. The amount of halogen introduced will generally be in the range from about 1 to 5 halogen atoms per molecule, depending on the reactivity of the resulting halide. On a weight percent basis, the amount of halide will generally range from about 1 to 25, more usually from about 1 to 10.
The halohydrocarbon and alklylene polyamine or polyalkylene polyamine may be brought together neat or in the presence of an inert solvent, particularly a hydrocarbon solvent. The inert hydrocarbon solvent may be aliphatic or aromatic. Also, aliphatic alcohols may be used by themselves or in combination with another solvent, when capable of dissolving the reactants.
The reaction may be carried out at room temperature C.), but elevated temperatures are preferred. Usually, the temperature will be in the range of from about 100 to 225 C. Depending on the temperature of the reaction, the particular halogen used, the mole ratios and the particular amine, as well as the reactant concentrations, the time may vary from 1 to 24 hours, more usually from about 3 to 20 hours. Times greatly in excess of 24 hours do not particularly enhance the yield and may lead to undesirable degradation. It is therefore preferred to limit the reaction time to fewer than 24 hours.
The mole ratio of halohydrocarbon to alkylene amine will generally be in the range from about 0.2 to 10 moles of alkylene amine per mole of halohydrocarbon, more usually 0.5 to 5 moles of alkylene amine per mole of halohydrocarbon. The mole ratio will depend upon the amount of halogen present in the halohydrocarbon, the particular halogen and the desired ratio of hydrocarbon to amine. If complete suppression of polysubstitution of the alkylene polyamines is desired, then large mole excesses of the amine will be used.
Small amounts of residual halogen in the final composition are not deleterious. Generally, the residual halogen as bound halogen will be in the range of 0 to 10 weight percent of the composition. Small amounts of halogen may be present as the hydrohalide salt of the hydrocarbon substituted alkylene polyamines.
Generally, the hydrocarbons used will have aliphatic unsaturation. In particular instances, the amines may react in a way resulting in the elimination of hydrogen halide, introducing further aliphatic unsaturation into the hydrocarbon radical. Therefore, the hydrocarbon radicals usually will be olefinically unsaturated. However, the olefinic unsaturation does not significantly affect the utility of the product, and when available, saturated aliphatic halide may be used.
After the reaction has been carried out for a sufiicient length of time, the reaction mixture may be extracted with a hydrocarbon medium to free the product from any low molecular weight amine salt which has formed. The product may then be isolated by evaporation of the solvent. Further separation from unreacted hydrocarbon or purification may be carried out as desired, e.g., chromatography.
Depending on the particular application of the composition of this invention, the reaction may be carried out in the medium in which it will ultimately find use and be formed at concentrations which provide a concentrate of the detergent composition. Thus, the final reaction mixture may be in a form to be used directly upon dilution in lubricating oils or fuels.
PREPARATION OF SPECIFIC COMPOSITIONS The following examples are olfered by Way of illustration and not by way of limitation.
Example A Into a reaction flask was introduced 950 g. of polyisobutylene (approximate molecular weight:950) dissolved in 1,000 ml. of carbon tetrachloride. The mixture was 8 stirred and chlorine was introduced at a rate of 235-250 ml. per minute, the temperature being maintained at 0 C. After the reaction mixture had taken up 51 g. of chlorine, the introduction of chlorine was terminated, the carbon tetrachloride removed in vacuo and the chlorinated polyisobutylene isolated.
Example B Into a reaction flask was introduced 225 g. of N- bromo-succinimide, 750 g. of polyisobutylene (approximately 930 average molecular weight) and 750 ml. of carbon tetrachloride, the flask swept with nitrogen and the solution heated to 70 C. while maintaining a positive nitrogen pressure on the flask. To the solution was then added dropwise 0.5 g. of benzoyl peroxide in 50 ml. of carbon tetrachloride. At the end of the addition, the solution was cooled and the succinimide filtered off. The carbon tetrachloride was removed in vacuo. Analysis: wt. percent bromine=8.86, 8.80.
Example 1 Into a reaction flask was introduced 873 g. of bromopolyisobutlylene (polyisobutylene of approximately 930 average molecular weight brominated to 4.93 weight percent bromine) and 87 g. of tetraethylene pentamine (a mixture of compounds having the average composition of tetraethylene pentamine). The reaction was stirred for one-half hour and then heated to 185 C. for about 18 hours. At the end of this time, the mixture was allowed to cool, diluted with 3 volumes of n-hexane, and the hydrobromide salt permitted to settle. The supernatant liquid was then decanted and the remaining salt extracted with ethanol and water. After evaporation of the volatile material, the final product analyzed as follows: wt. percent nitrogen=l.1; wt. percent bromine=0.2.
Example 2 Into a reaction flask was introduced 800 g. of a chlorinated paraflinic base oil (average molecular weight approximately 570 chlorinated to approximately 6.4 weight percent) and g. of tetraethylene pentamine and the mixture heated at 185 C. for 6 hours. At the end of this time, the reaction mixture was cooled and diluted with 3 volumes of n-hexane and 1 volume of ethanol followed by dilute sodium carbonate and water washes. The mixture was then heated to reflux and dilute sodium carbonate added until the cloud point was reached, the phases were separated, the organic phase diluted with one volume of ethanol, and then the mixture extracted with water. The volatile products were then pumped from the organic phase. Analysis: wt. percent N=0.53; wt. percent basic N=0.36.
Example 3 Into a reaction flask was introduced 1,780 g. of brominated polyisobutylene (polyisobutylene of approximately 930 average molecular weight brominated to 8.6 weight percent bromine) and 350 g. of a mixture of polyethylene amines having an average composition of tetraethylene pentamine and allowed to stand overnight at ambient temperatures. The mixture was then heated at 150 C. for several hours (approximately 5 to 6), cooled and diluted with several volumes of n-pentane and allowed to stand. The solution was then concentrated to about one-half its original volume, about 1 liter of ethanol and about 1 liter of 10 percent aqueous sodium carbonate added. The phases were separated and the sodium carbonate extraction repeated, followed by washing the hexane phase with water. Volatile materials were removed in vacuo by heating the organic phase to C., leaving a residue of 1,369 g. Analysis: wt. percent nitrogen=2.26, 2.21; wt. percent basic nitrogen=1.09; wt. percent bromine=1.08, 0.99; molecular wt.=2,318 (determined by ThermoNAM, a differential vapor pressure technique).
Example 4 Into a reaction flask was introduced 433 g. of chlorinated polyisobutylene (polyisobutylene of approximately 950 average molecular weight chlorinated to 9.3 weight percent chlorine) and 240 g. of alkylene polyamine having an average composition of tetraethylene pentamine and 640 ml. of benzene added. The mixture was heated to reflux and the benzene distilled off. The residue was then heated at 150 C. for 4 hours. After cooling the reaction mixture and diluting with mixed hexanes, 200 ml. of ethanol was added and the organic phase extracted with 10 weight percent aqueous sodium carbonate, the phases separated and the extraction of the organic phase repeated, the phases separated again and finally the organic phase washed with water. The volatile materials were then removed in vacuo. Analysis: wt. percent nitrogen=4.66, 4.76; wt. percent chlorine=3.16; molecular wt. (ThermoNAM) 1,318.
Example 5 Into a pressure vessel was introduced 1,500 ml. of a solution of 5 parts of chlorinated polyisobutylene (approximately 1,300 molecular weight) and 2 parts of benzene (the solution analyzing to 3.66 weight percent chlorine) and 300 g. of ethylene diamine (the vessel sealed and heated at 150 C. with rocking overnight). The vessel was then allowed to cool, vented and to the reaction mixture was added an equal volume of n-hexane and a one-third volume of ethanol, the resulting mixture being heated to reflux. Approximately one-third volume of water was then added, the phases separated and the hydrocarbon phase isolated. The volatile materials were removed in vacuo (and the residue analyzed). Analysis: wt. percent nitrogen=1.82, 1.83; wt. percent basic nitrogen=1.65, 1.63.
Example 6 Into a reaction flask was introduced 3,000 g. of a 70 weight percent solution in benzene of chloropolyisobutylene (polyisobutylene of approximately 1,300 molecular weight chlorinated to 4.3 weight percent chlorine) and 210 g. of alkylene polyamine having an average composition of triethylene tetramine and the mixture heated to reflux, the benzene stripped off and the mixture further heated at 170 C. for 4 hours. At the end of this time, the mixture was allowed to cool, and then diluted with equal volumes of mixed hexanes and absolute ethanol, heated to reflux and then one-third volume of weight percent aqueous sodium carbonate added. The phases Were separated, and the organic phase washed with water and then the volatile materials removed in vacuo. Analysis: wt. percent nitrogen=1.44; wt. percent basic nitrogen=0.89; wt. percent chlorine=1.45; molecular weight (Thermo NAM)=2,419, 2,371.
Example 7 Following the procedure described in Example 6, 1,500 g. of a 70 weight percent solution in benzene of chloropolyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to -10 weight percent) and 155 g. of diethylene triamine were combined. Analysis: wt. percent nitrogen=l.59, 1.60; wt. percent basic nitrogen=0.96, 0.97.
Example 8 Into a reaction flask was introduced 800 g. of benzene, 846 g. of chlorinated polyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight percent) and 300 g. of alkylene polyamine having an average composition of triethylene tetramine and the mixture heated to reflux and benzene gradually stripped oil. The temperature was then increased to 175 C. and maintained for 3.5 hours. After allowing the mixture to cool, equal volumes of both mixed hex-anes and 95 percent ethanol were added and the resulting solution separated into 2 equal portions. One of the portions was allowed to sit in a separatory funnel and the alcoholic phase permitted to separate. The hydrocarbon portion was separated from the alcoholic portion, washed with 10 weight percent aqueous sodium carbonate, followed by washing with water, and the volatile materials then removed in vacuo. Analysis: wt. percent nitrogen=3.03, 3.06; wt. percent basic nitrogen=2.26, 2.28.
Example 9 Into a reaction flask was introduced 600 g. of chloropolyisobutylene (polyisobutylene of approximately 950 molecular weight chlorinated to 5.6 weight percent), 550 m1. of benzene and 220 g. of alkylene polyamine of the average composition of triethylene tetramine and the mixture allowed to stand at ambient temperatures for 2 days. The benzene was then distilled ofl, and the temperature of the mixture raised to C. and maintained for 4 hours. The usual extraction procedure using mixed hexanes and ethanol, followed by sodium carbonate and water washes was carried out and the volatile materials then removed in vacuo. Analysis: wt. percent nitrogen: 4.10, 4.05; wt. percent basic nitrogen=3.07; wt. percent chlorine=0.57; molecular wt. (ThermoNAM)=1,5l0.
Example 10 Following the procedures of the previous examples, 1,500 g. of chloropolyisobutylene (polyisobutylene of approximately 2,700 molecular weight chlorinated to 6.11 weight percent chlorine) was combined with 350 g. of alkylene polyamine having an average composition of tetraethylene pentamine in one liter of benzene. Analysis: wt. percent nitrogen=1.53, 1.53.
Example 11 Following the procedures of the previous examples, 1,423 g. of chloropolyisobutylene (polyisobutylene of approximately 950 average molecular weight chlorinated to approximately 5 weight percent chlorine) was combined with 286 g. of an alkylene polyamine having an average composition of nonaethylene decamine (DowAmine 400 provided by the Dow Chemical Co.) in 1.4 liters of benzene. Analysis: wt. percent nitrogen=4.14, 4.20.
Example 12 Following the procedure of the previous examples, 600 g. of chloropolyisobutylene (polyisobutylene of approximately 2,700 average molecular weight chlorinated to about 2 weight percent chlorine) was combined with 40 g. of alkylene polyamine having an average composition of tetraethylene pentamine in 540 ml. of benzene. Analysis: wt. percent nitrogen=0.99; molecular weight (ThermoNAM) =approximately 4,400.
As already indicated, the compositions of this invention find a wide variety of uses under a wide variety of conditions. The subject compositions find use as detergents and dispersants in lubricating oils for internal combustion engines, automobile engines, in two-cycle engines, as well as in fuels for internal combustion engines, particularly gasoline engines.
UTILITY Preferred compositions which find use in lubricating oils, both for the automobile and the diesel engines, will for the most part have the following formula:
U is alkylene of from 2 to 3 carbon atoms, preferably ethylene;
a is an integer of from 1 to 5, more usually from 2 to 4;
c is an integer or fractional number in the range of from 1 to 3, more usually in the range of 1 to 2, and equal to or less than the number of amine nitrogen atoms,
preferably on the average less than the number of amine nitrogen atoms; and
R is a branched chain aliphatic hydrocarbon radical derived by polymerization of olefins of from 3 to 4 carbon atoms and of from about 700 to 3,000 molecular weight, more usually from about 750 to 2,800 average molecular weight. The preferred R groups are polypropylene and polyisobutylene.
The detergents may be prepared as concentrates having as high as 80 weight percent of the detergent in lubricating oil. Generally, concentrates will vary from about to 80 weight percent. However, when the oil is to be used in the engine, the amount of the detergent generally will vary from about 0.1 to weight percent, more usually from 0.25 to 10 Weight percent. The lubricating oil compositions may therefore vary in the amount of detergent from 0.1 to 80 weight percent.
The compositions of this invention can be used with various base oils which find use as lubricating oils. Naturally occurring base oils include naphthenic base, parafiin base, asphaltic base and mixed base lubricating oils. Synthetic hydrocarbon oils include alkylene polymers, such as polymers of propylene, butylene, l-octene, and mixtures thereof and alkylated aromatic hydrocarbons. Nonhydrocarbon lubricating oils include: alkylene oxide type polymers; carboxylic acid esters such as octyl adipate, nonyl azelate, decyl suberate, butyl alkenylsuccinate, etc.; also, inorganic esters such as phosphates and silicates.
The above base oils may be used individually or in combination, whenever miscible or made so by the use of mutual solvents.
Preferably, the detergents of this invention are used in lubricating oils with an oxidation inhibitor and extreme pressure agent. The preferred inhibitors are metal dithiophosphates, particularly zinc 0,0-di(hydrocarbyl) phosphorodithioate, where the hydrocarbyl groups are generally from 4 to 36 carbon atoms. (Hydrocarbyl is an organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof, e.g., aralkyl or alkaryl, and may be aliphatically saturated or unsaturated, e.g., ethylenic unsaturation.) Preferably, the hydrocarbyl groups are alkyl or alkaryl groups. Also, S-alkyl and S-polyalkyleneoxy esters of the phosphorodithioate may be used. Usually, about 6 to 50 mM./kg. of the phosphorodithioate is used in the oil.
Other additives may also be included in the lubricating oil. These additives include pour point depressants, viscosity index improvers, antiwear agents, rust inhibitors, corrosion inhibitors, other detergents and dispersants, etc. Generally, the total amount of additives exclusive of the detergent will be in the range of from about 0.1 to 5 weight percent of the lubricating oil composition.
A special situation in which the detergents of this invention are employed in lubricating oils are lubricating oils for two-cycle engines. In the two-cycle engine, the oil is incorporated with the fuel and burned directly in the piston chamber.
Preferred compositions for use in the two-cycle engine oil have the following formula:
wherein:
U is alkylene of from 2 to 3 carbon atoms, preferably ethylene;
a is an integer of from 1 to 4, preferably 2 to 4;
0 is an integer or fractional number of from 1 to 2,
preferably of from 1 to 1.5; and
R is a branched chain aliphatic hydrocarbon radical derived from a polyolefin obtained from olefins of from 3 to 4 carbon atoms and having a molecular weight in the range of about 650 to 3,000, more usually from about 750 to 2,000. The preferred polymers are polypropylene and polyisobutylene.
Generally, hydrocarbonaceous lubricating oils will be used, particularly petroleum derived, such as the mixed base, parafiinic and naphthenic base oils. Moreover, in place of phosphorodithioate inhibitors, other oxidative inhibitors such as bis(phenols), etc. may be used. When phosphorodithioate additives are used, concentrations in the oil may be as low as one mM./kg. Finally, a halide scavenger for the lead may also be added, usually to enhance the halide already present in the gasoline. Alkylene halide scavengers such as ethylene dibromide may be used with the detergent compositions of this invention, but aryl halides, e.g., dichlorobenzene, are preferred. Other additives, already described for the lubricating oils, may also be included.
EVALUATION In order to demonstrate the wide applicability of the compounds within the scope of this invention, various compounds were tested under a wide variety of conditions simulating a variety of situations in which lubricating oils are used. Three different engine tests were carried out of varying severity and varying demands on detergents to demonstrate the excellent elfectiveness of the compositions of this invention in lubricating oils.
The first test was the L-l Supp. 1 (MIL-L-2l04B, Supp. 1 Specifications). The oil was formulated containing 0.03 weight percent nitrogen and 8 mM./kg. of 0,0- dialkyl phosphorodithioate (alkyl of from 4 to 6 carbon atoms) in a Mid-Continent SAE 30 base oil. The test was carried out for 120 hours, the following table indicating the results.
TABLE I Grooves l Lands 3 Example: 1 4-0. 5-0-0 -0-75 2 4-1-2-1 435--25 Base oil 3 38-18-10-10 3 800-800-800 1 Measured on a rating of 0 to 100, 100 being completely filled. 2 Measured on a rating of 0 to 800, 800 being completely black. 3 Tested under the less severe L-1 conditions (MIL-L-2l04A).
1 Used the same rating as in Table I. 2 Rated 0 to 10, 10 being completely clean.
As a further test of the usefulness of the compositions of this invention in lubricating oils, a modified FL-2 test procedure, as described in June 21, 1948 report of the Coordinating Research Council, was employed. This test simulates automobile engine performance. A standard procedure requires the maintenance of a jacket temperature of 95 F. and a crankcase oil temperature of 155 F.
The Yamaha engine test uses a 75 cc. Model YG-1 motorcycle engine. The same conditions as described for the McCulloch engine are also used for the Yamaha engine.
The following table indicates the results obtained with a Variety of detergents in the McCulloch engine and in the Yamaha engine tests.
TABLE IV Wt. percent Ring in oil of sticking G.D. No. Land dep. candidate Exh. Piston Total detergent PV 1 Top 2nd Top 2nd Top 2nd ports 4 und. rating McCulloch 7 2 360 6 500 250 5 8. 3 37. 6 9 .5 360 8 700 640 7 7.8 30.8 Base 011 4 360 580 610 10 6. 0 28. 7
Yamaha Example 5 7 .6 360 F 10 640 620 12 6 2 30. 2 Base oil .0 360 160 700 750 15 1 4 19. 6
1 PVpiston varnish, 0-10, 10 being clean.
2 GD. No.-groovc deposit number, 0-10, 10 being clean. 3 Land dep.1and deposit number, 0-800, 800 being black. Exh. ports-exhaust ports. 0100% blocked.
5 Piston und.piston underhcad, 0-10, 10 being clean.
at 2,500 r.p.m. and 45 brake horsepower for 40 hours (closely simulating the relatively cold engine conditions which are normally experienced in city driving). At the end of each test, the engine is dismantled and the amount of total sludge (rating of 0 to 50, no sludge being 50) and clogging of the rings and oil screen (rating of 0 to 100, no clogging being 0) is determined. Also, the piston varnish is rated (rating of 0 to 10, no varnish being 10) and the total varnish is evaluated (rating of 0 to 50, no varnish being 50). The above test was modified by increasing the time and periodically raising the oil sump temperature from 165 F. to 205 F. and the water jacket temperature from 95 to 170 F.
Using a Mid-Continent SAE base stock, each condidate detergent was employed at concentrations to provide a constant weight percent of nitrogen; also included in the oil was 10 mM./kg. of zinc 0,0di(alkyl) dithiophos- It is evident from the foregoing results that the compositions of this invention, having a wide variety of structures and a wide variation in hydrocarbon to amine nitrogen ratio, provide effective detergency and dispersancy under a great variety of conditions. Not only are they eflective in the lubricating oils of the automobile engine and in the much hotter conditions in the diesel engine, but they are also effective in two-cycle engines as well. Universality of detergency is only difiiculty achieved and, of course, certain snbgenera within the subject invention will operate more eifectively under some conditions than they will under others. Therefore, as indicated, for particular uses narrower snbgenera are preferred.
For a description of the effectiveness of the compositions of this invention as fuel detergents, reference is made to U.S. Pat. No. 3,438,757, which issued on Apr. 15, 1969.
We claim:
1. A composition of the formula:
phate (alkyl of from 4 to 6 carbon atoms) and 2 mM./ (CHM kg. of zinc 0,0di(alkylphenyl) dithiophosphate (alkyl t: L U H is polypropylene of from 12 to 15 carbon atoms). The N following table indicates the results obtained. (OHM TABLE III Wt. percent of Clogging candidate Piston Total Total Time,
Example: detergent varnish varnish sludging Ring Screen hrs.
1 Base oil 1 1 Engine stopped in approximately 12 hours because it was unable to run any further.
The results demonstrate that the branched chain hydrocarbon substituted polyamines provide excellent versatility in providing detergency and dispersancy under broad gines were used: a Yamaha engine which is used on motorcycles, and a McCulloch engine which is used for chain saws.
In the McCulloch engine test, the engine is a Model 1-81 approximately 85 cc. displacement. The test is carried out for 10 hours, the engine being run at 7,000 r.p.m., at a temperature of 435 F. and with a wide open throttle. Using regular gasoline, a fuel-oil mixture in the ratio of 20:1 is prepared, the oil composition being a blend of detergent in SAE 40 grade base oil, such that wherein:
U is alkylene of from 2 to 6 carbon atoms;
a is an integer of from 0 to 10;
b is an integer of from 0 to 1;
(1+2!) is an integer of from 1 to 10;
c is an integer or fractional number in the range of 1 to 5, and equal to or less than the number of nitrogen atoms in the molecule; and
R is of from 40 to 300 carbon atoms and is an aliphatic or alicyclic branched chain hydrocarbon radical derived from petroleum hydrocanbons or polyolefins of monomers from 2 to 6 carbon atoms, with the proviso that when the monomer is ethylene, it is copolymerized with a higher homologue.
2. A composition according to claim 1, wherein:
a is of from 1 to 6;
the finished oil contained 0.126 weight percent nitrogen. a+2b is of from lto 6;
15 c is of from 1 to 3; and R is a polyolefin of from 50 to 200 carbon atoms.
3. A composition according to claim 1, wherein: b is and R is a polyolefin derived from olefins of from 3 to 4 carbon atoms. 4. A composition of the formula:
U is alkylene of from 2 to 3 carbon atoms;
a is an integer of from 1 to 5;
c is an integer of from 1 to 5 and, on the average, equal to or less than the number of nitrogen atoms; and
R is of from about 600 to 2,800 average molecular weight and is a branched chain aliphatic hydrocarbon polyolefin derived from olefins of from 2 to 6 carbon atoms, with that proviso that when the monomer is ethylene, it is copolymerized with a higher homologue. 5. A composition according to claim 4, wherein:
a is of from 1 to 4;
c is of from 1 to 3; and
R is a polyolefin derived from olefins of from 3 to 4 carbon atoms, and of about 600 to 2,800 average molecular weight. 6. A composition according to claim 5, wherein R is of from about 750m about 2,000 molecular weight.
7. A composition according to claim 4, wherein c is one.
8. A composition according to claim 4, wherein c is in the range of about 1.25 to 3.
9. A composition of the formula:
wherein:
a is in the range of 1 to 5;
c is in the range of 1 to 4 and equal to or less than the number of nitrogen atoms; and
R is a branched chain aliphatic hydrocarbon group derived from olefins of from 3 to 4 carbon atoms and of an average molecular weight in the range of about 650 to 2,800. 10. A composition according to claim 9, wherein:
a is in the range of 1 to 4;
c is in the range of 1 to 2; and
R is polypropenyl or polyisobutenyl of from about 750 to 2,000'molecular weight. 11. A polyisobutenyl ethylene diamine having from 1 to 2 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
12. A polyisobutenyl ethylene diamine having about 1 polyisobutenyl group of from about 650 to 2,800 average molecular weight.
13. A polypropenyl ethylene diamine having from 1 to 2 polypropenyl groups of from about 650 to 2,800 average molecular weight.
14. A polyisobutenyl diethylene triamine having from 1 to 2 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
15. A polypropenyl diethylene triamine having from 1 to 2 polypropenyl groups of from about 650 to 2,800 average molecular weight.
16. A polyisobutenyl triethylene tetramine having from 1 to 3 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
17. A polypropenyl triethylene tetramine having from 1 to 3 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
18. A polyisobutenyl tetraethylene pentamine having from 1 to 3 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
19. A polypropenyl tetraethylene pentamine having from 1 to 3 polyisobutenyl groups of from about 650 to 2,800 average molecular weight.
20. A lubricating oil composition having from 0.1 to weight percent of a composition according to claim 1 and an oil of lubricating viscosity.
21. A lubricating oil composition having from 10 to 80 weight percent of a composition according to claim 1 and an oil of lubricating viscosity.
22. A lubricating oil composition having from 0.1 to 80 weight percent of a composition according to claim 4 and an oil of lubricating viscosity.
23. A lubricating oil composition having from 0.1 to 80 weight percent of a composition according to claim 9 and an oil of lubricating viscosity.
References Cited UNITED STATES PATENTS 3,275,554 9/1966 Wagenaar 25250 3,438,757 4/1969 Honnen et al 4472X 3,454,555 7/1969 Van der Voort et al. 252-50X 3,485,601 12/1969 Mehtnedbasich 4472X PATRICK P. GARVIN, Primary Examiner US. Cl. X.R.
US23959A 1965-08-23 1970-03-30 Lubricating oil additives Expired - Lifetime US3565804A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US48191665A 1965-08-23 1965-08-23
US48877565A 1965-09-20 1965-09-20
US53857166A 1966-03-30 1966-03-30
US64761167A 1967-06-21 1967-06-21
US2395970A 1970-03-30 1970-03-30

Publications (1)

Publication Number Publication Date
US3565804A true US3565804A (en) 1971-02-23

Family

ID=27534049

Family Applications (3)

Application Number Title Priority Date Filing Date
US488775A Expired - Lifetime US3574576A (en) 1965-08-23 1965-09-20 Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
US647611A Expired - Lifetime US3438757A (en) 1965-08-23 1967-06-21 Hydrocarbyl amines for fuel detergents
US23959A Expired - Lifetime US3565804A (en) 1965-08-23 1970-03-30 Lubricating oil additives

Family Applications Before (2)

Application Number Title Priority Date Filing Date
US488775A Expired - Lifetime US3574576A (en) 1965-08-23 1965-09-20 Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
US647611A Expired - Lifetime US3438757A (en) 1965-08-23 1967-06-21 Hydrocarbyl amines for fuel detergents

Country Status (7)

Country Link
US (3) US3574576A (en)
JP (1) JPS4945685B1 (en)
BE (1) BE744693Q (en)
DE (2) DE1545487C3 (en)
FR (2) FR1489559A (en)
GB (2) GB1083610A (en)
MY (1) MY7000109A (en)

Cited By (464)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3671511A (en) * 1970-04-23 1972-06-20 Lewis R Honnen Process for preparing polyolefin-substituted amines
US3844958A (en) * 1965-08-23 1974-10-29 Chevron Res Hydrocarbyl amines for lubricating oil detergents
US3996024A (en) * 1973-06-22 1976-12-07 Chevron Research Company Fuel composition
US4022589A (en) * 1974-10-17 1977-05-10 Phillips Petroleum Company Fuel additive package containing polybutene amine and lubricating oil
US4100086A (en) * 1976-10-26 1978-07-11 Texaco Inc. Dispersant and lube oils containing same
DE2937677A1 (en) * 1978-09-18 1980-04-03 Exxon Research Engineering Co LUBRICANT PREPARATION
US4200518A (en) * 1979-03-22 1980-04-29 Chevron Research Company Heat exchanger anti-foulant
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
US4746447A (en) * 1986-01-10 1988-05-24 Chevron Research Company Carbonate treated hydrocarbyl-substituted polyamines
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US4877416A (en) * 1987-11-18 1989-10-31 Chevron Research Company Synergistic fuel compositions
EP0351964A1 (en) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
US4973336A (en) * 1988-06-10 1990-11-27 Gheysens Jean Louis G Fuel additives
WO1992021736A1 (en) 1991-05-30 1992-12-10 The Lubrizol Corporation Two-cycle lubricant and method of using same
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
EP0568873A2 (en) * 1992-05-04 1993-11-10 BASF Aktiengesellschaft Beta-aminonitriles and N-alkyl-1,3-propylenediamines as well as their use as fuel and lubricant additives
US5292444A (en) * 1992-10-02 1994-03-08 Exxon Research And Engineering Company Lube oil compositions containing fullerene-grafted polymers
US5292813A (en) * 1992-10-02 1994-03-08 Exxon Research & Engineering Co. Fullerene-grafted polymers and processes of making
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
EP0611818A1 (en) 1990-07-31 1994-08-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same
WO1994024231A1 (en) * 1993-04-22 1994-10-27 Basf Aktiengesellschaft Poly-1-n-alkene amines and motor fuel and lubricant compositions containing them
EP0639589A1 (en) * 1993-08-19 1995-02-22 Ferro Corporation Process for the production of fuel additives from chlorinated polybutenes
US5430105A (en) * 1992-12-17 1995-07-04 Exxon Chemical Patents Inc. Low sediment process for forming borated dispersant
US5455358A (en) * 1992-02-10 1995-10-03 Chevron U.S.A. Inc. Fuel compositions containing alkyl-substituted cyclic urea-substituted amines
US5457211A (en) * 1992-02-10 1995-10-10 Chevron U.S.A. Inc. Hydroxyalkyl-substituted cyclic urea-substituted amines
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
US5478367A (en) * 1991-10-11 1995-12-26 Exxon Chemical Patents Inc. Fuel oil compositions
EP0695798A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
EP0695799A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Combination of a sulfer compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5558802A (en) * 1995-09-14 1996-09-24 Exxon Chemical Patents Inc Multigrade crankcase lubricants with low temperature pumpability and low volatility
EP0769546A2 (en) 1995-10-18 1997-04-23 The Lubrizol Corporation Antiwear enhancing composition for lubricants and functional fluids
US5652202A (en) * 1995-08-15 1997-07-29 Exxon Chemical Patents Inc. Lubricating oil compositions
US5810894A (en) * 1996-12-20 1998-09-22 Ferro Corporation Monoamines and a method of making the same
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
US5945388A (en) * 1993-09-23 1999-08-31 Lubrizol Adibis Holdings (Uk) Ltd. Lubricating oil compositions
WO2000009634A1 (en) * 1998-08-10 2000-02-24 The Associated Octel Company Limited Diesel fuel compositions
US6066603A (en) * 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US6071319A (en) * 1998-12-22 2000-06-06 Chevron Chemical Company Llc Fuel additive compositions containing aromatic esters of polyalkylphenoxyalkanols and aliphatic amines
US6136051A (en) * 1995-07-06 2000-10-24 Chevron Chemical Company Method and composition for reduction of combustion chamber deposits
EP1057811A1 (en) * 1999-06-02 2000-12-06 Chevron Chemical Company LLC Polyalkylpyrrolidines and fuel compositions containing the same
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof
US6299655B1 (en) * 1985-03-14 2001-10-09 The Lubrizol Corporation Diesel fuel compositions
WO2002010276A2 (en) 2000-07-31 2002-02-07 The Lubrizol Corporation Polymeric mixture useful as viscosity improver for lubricating oils
US6346129B1 (en) 1990-12-27 2002-02-12 Chevron Oronite Company Llc Fuel compositions containing hydroxyalkyl-substituted polyamines
US6423670B2 (en) 2000-03-20 2002-07-23 Infineum International Ltd. Lubricating oil compositions
US20020193650A1 (en) * 2001-05-17 2002-12-19 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US6525004B1 (en) 2001-05-01 2003-02-25 Infineum International Inc. Combustion improving additive for small engine lubricating oils
US20030079399A1 (en) * 2001-09-14 2003-05-01 Malfer Dennis J. Fuels compositions for direct injection gasoline engines
US6573223B1 (en) 2002-03-04 2003-06-03 The Lubrizol Corporation Lubricating compositions with good thermal stability and demulsibility properties
US20030122104A1 (en) * 2001-02-12 2003-07-03 Dober Chemical Corporation Liquid replacement systems
EP1331376A2 (en) 2002-01-23 2003-07-30 Chevron Oronite Company LLC Method for removing engine deposits in a reciprocating internal combustion engine
US20030173251A1 (en) * 2000-12-22 2003-09-18 Antonio Gutierrez Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US6660050B1 (en) 2002-05-23 2003-12-09 Chevron U.S.A. Inc. Method for controlling deposits in the fuel reformer of a fuel cell system
US6689723B2 (en) 2002-03-05 2004-02-10 Exxonmobil Chemical Patents Inc. Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same
US20040033908A1 (en) * 2002-08-16 2004-02-19 Deckman Douglas E. Functional fluid lubricant using low Noack volatility base stock fluids
US20040091654A1 (en) * 2001-08-24 2004-05-13 Fleetguard, Inc. Controlled release of additives in cooling systems
US6827750B2 (en) 2001-08-24 2004-12-07 Dober Chemical Corp Controlled release additives in fuel systems
US6835218B1 (en) 2001-08-24 2004-12-28 Dober Chemical Corp. Fuel additive compositions
US20050019236A1 (en) * 2001-08-24 2005-01-27 Harold Martin Controlled release of additives in fluid systems
US6860241B2 (en) 1999-06-16 2005-03-01 Dober Chemical Corp. Fuel filter including slow release additive
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050065044A1 (en) * 2001-05-08 2005-03-24 Migdal Cyril A Nanosized particles of molybdenum sulfide and derivatives,method for its preparation and uses thereof as lubricant additive
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
US7001531B2 (en) 2001-08-24 2006-02-21 Dober Chemical Corp. Sustained release coolant additive composition
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
US20060196111A1 (en) * 2005-03-04 2006-09-07 Colucci William J Fuel additive composition
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US20060205615A1 (en) * 2005-03-14 2006-09-14 Esche Carl K Jr Additives and lubricant formulations for improved antioxidant properties
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
US20070049503A1 (en) * 2005-08-31 2007-03-01 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US20070111908A1 (en) * 2004-07-19 2007-05-17 Lam William Y Titanium-containing lubricating oil composition
US20070111906A1 (en) * 2005-11-12 2007-05-17 Milner Jeffrey L Relatively low viscosity transmission fluids
US20070132274A1 (en) * 2005-12-09 2007-06-14 Lam William Y Titanium-containing lubricating oil composition
US20070135317A1 (en) * 2005-12-12 2007-06-14 Tze-Chi Jao Nanosphere additives and lubricant formulations containing the nanosphere additives
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US20070254820A1 (en) * 2006-04-28 2007-11-01 Tze-Chi Jao Diblock monopolymers as lubricant additives and lubricant formulations containing same
US20070259792A1 (en) * 2006-03-22 2007-11-08 Null Volker K Functional fluid compositions
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
WO2008013698A1 (en) 2006-07-21 2008-01-31 Exxonmobil Research And Engineering Company Method for lubricating heavy duty geared apparatus
US20080026973A1 (en) * 2006-05-03 2008-01-31 Nelson David C Lubricating oil composition
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
US20080108531A1 (en) * 2006-11-08 2008-05-08 The Lubrizol Corporation Viscosity Modifiers in Controlled Release Lubricant Additive Gels
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
WO2008060888A2 (en) 2006-11-09 2008-05-22 The Lubrizol Corporation Quaternary ammonium salt of a polyalkene-substituted amine compound
US20080132432A1 (en) * 2006-12-01 2008-06-05 Mathur Naresh C Additives and lubricant formulations for providing friction modification
EP1930401A1 (en) 2006-11-21 2008-06-11 Chevron Oronite Company LLC Functional fluids comprising alkyl toluene sulfonates
US20080139429A1 (en) * 2006-12-06 2008-06-12 Guinther Gregory H Titanium-containing lubricating oil composition
US20080161213A1 (en) * 2007-01-03 2008-07-03 Tze-Chi Jao Nanoparticle additives and lubricant formulations containing the nanoparticle additives
EP1942177A2 (en) 2006-12-19 2008-07-09 Chevron Oronite Company LLC Lubricating oil providing enhanced piston cleanliness
DE102007056248A1 (en) 2006-12-08 2008-07-10 Afton Chemical Corp. Additive and lubricant formulations for improved antiwear properties
EP1947164A1 (en) 2006-12-21 2008-07-23 Chevron Oronite Technology B.V. Engine lubricant with enhanced thermal stability
US20080182768A1 (en) * 2007-01-31 2008-07-31 Devlin Cathy C Lubricant composition for bio-diesel fuel engine applications
EP1959003A2 (en) 2007-02-08 2008-08-20 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
DE102008005874A1 (en) 2007-03-15 2008-09-18 Afton Chemical Corp. Additive and lubricant formulations for improved antiwear properties
DE102007061422A1 (en) 2007-03-26 2008-10-02 Afton Chemical Corp. Lubricating oil composition for improved oxidation, viscosity increase, oil consumption and piston deposition control
US20080280796A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved catalyst performance
DE102008009042A1 (en) 2007-05-08 2008-11-13 Afton Chemical Corp. Additive and lubricant formulations for improved phosphorus retention properties
US20080296234A1 (en) * 2001-08-24 2008-12-04 Dober Chemical Corporation Controlled release of microbiocides
EP2000523A1 (en) 2007-05-30 2008-12-10 Chevron Oronite S.A. Lubricating oil with enhanced protection against wear and corrosion
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
US20090042752A1 (en) * 2007-08-09 2009-02-12 Malcolm Waddoups Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters
US20090069205A1 (en) * 2007-09-10 2009-03-12 Devlin Mark T Additives and lubricant formulations having improved antiwear properties
EP2042582A2 (en) 2007-09-24 2009-04-01 Afton Chemical Corporation Surface passivation and to methods for the reduction of fuel thermal degradation deposits
US20090111722A1 (en) * 2007-10-25 2009-04-30 Guinther Gregory H Engine wear protection in engines operated using ethanol-based fuel
US20090143265A1 (en) * 2007-11-30 2009-06-04 Ellington Joruetta R Additives and lubricant formulations for improved antioxidant properties
US20090156445A1 (en) * 2007-12-13 2009-06-18 Lam William Y Lubricant composition suitable for engines fueled by alternate fuels
EP2075264A1 (en) 2007-12-26 2009-07-01 Infineum International Limited Method of forming polyalkene substituted carboxylic acid compositions
EP2077316A2 (en) 2007-12-17 2009-07-08 Infineum International Limited Lubricant compositions with low HTHS for a given SAE viscosity grade
EP2083024A1 (en) 2008-01-24 2009-07-29 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2083063A1 (en) 2008-01-22 2009-07-29 Infineum International Limited Lubricating oil composition
EP2090642A1 (en) 2008-02-08 2009-08-19 Infineum International Limited Engine lubrication
US20090233822A1 (en) * 2008-03-11 2009-09-17 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
DE102009001301A1 (en) 2008-03-11 2009-09-24 Volkswagen Ag Method for lubricating a component only for the clutch of an automatic transmission, which requires lubrication
WO2009119831A1 (en) 2008-03-28 2009-10-01 富士フイルム株式会社 Composition and method for forming coating film
DE102009012567A1 (en) 2008-03-11 2009-10-01 Afton Chemical Corp. Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
EP2116590A1 (en) 2005-02-18 2009-11-11 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
US20090294345A1 (en) * 2008-05-27 2009-12-03 Dober Chemical Corporation Controlled release of microbiocides
US20090301968A1 (en) * 2008-05-27 2009-12-10 Dober Chemical Corporation Devices and methods for controlled release of additive compositions
US20090304868A1 (en) * 2008-05-27 2009-12-10 Dober Chemical Corporation Controlled release cooling additive composition
DE102009019952A1 (en) 2008-05-23 2009-12-10 Afton Chemical Corp. Controlled release of additives in lubricant compositions for gas turbines
EP2135925A1 (en) 2008-06-18 2009-12-23 Afton Chemical Corporation Method for making a titanium-containing lubricant additive
US20090318319A1 (en) * 2008-06-23 2009-12-24 Afton Chemical Corporation Friction modifiers for slideway applications
US20100004382A1 (en) * 2008-07-01 2010-01-07 Exxonmobil Research And Engineering Company Emulsion compositions with a polymeric emulsifier
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
US20100024286A1 (en) * 2008-07-31 2010-02-04 Smith Susan Jane Liquid fuel compositions
US20100024287A1 (en) * 2008-07-31 2010-02-04 Smith Susan Jane Liquid fuel compositions
US20100035774A1 (en) * 2008-08-08 2010-02-11 Afton Chemical Corporation Lubricant additive compositions having improved viscosity index increase properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
US20100144563A1 (en) * 2008-12-09 2010-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
WO2010091069A1 (en) 2009-02-05 2010-08-12 Butamax™ Advanced Biofuels LLC Gasoline deposit control additive compositions
US20100206260A1 (en) * 2009-02-18 2010-08-19 Chevron Oronite Company Llc Method for preventing exhaust valve seat recession
WO2010093519A1 (en) 2009-02-16 2010-08-19 Chemtura Corporation Fatty sorbitan ester based friction modifiers
WO2010096325A1 (en) 2009-02-18 2010-08-26 The Lubrizol Corporation Amine derivatives as friction modifiers in lubricants
EP2236590A1 (en) 2009-04-01 2010-10-06 Infineum International Limited Lubricating oil composition
WO2010115594A1 (en) 2009-04-07 2010-10-14 Infineum International Limited Marine engine lubrication
EP2243816A1 (en) 2003-06-25 2010-10-27 The Lubrizol Corporation Gel additives for fuel that reduce soot and/or emissions from engines
EP2251401A2 (en) 2009-05-15 2010-11-17 Afton Chemical Corporation Lubricant formulations and methods
US20100292112A1 (en) * 2009-05-14 2010-11-18 Afton Chemical Corporation Extended drain diesel lubricant formulations
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
EP2261311A1 (en) 2009-06-10 2010-12-15 Afton Chemical Corporation Lubricating method and composition for reducing engine deposits
WO2010147993A1 (en) 2009-06-16 2010-12-23 Chevron Phillips Chemical Company Lp Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends
WO2010149712A1 (en) 2009-06-25 2010-12-29 Shell Internationale Research Maatschappij B.V. Lubricating composition
EP2278327A1 (en) 2009-07-24 2011-01-26 Chevron Oronite S.A. System and Method for Screening Liquid Compositions
US7883638B2 (en) 2008-05-27 2011-02-08 Dober Chemical Corporation Controlled release cooling additive compositions
WO2011017186A1 (en) 2009-08-04 2011-02-10 The Lubrizol Corporation Compositions with fast and slow release components
EP2284248A2 (en) 2002-07-16 2011-02-16 The Lubrizol Corporation Slow release lubricant additives gel
EP2290041A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
US20110053814A1 (en) * 2009-09-02 2011-03-03 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
WO2011026990A1 (en) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Lubricating compositions
US20110067662A1 (en) * 2009-09-22 2011-03-24 Afton Chemical Corporation Lubricating oil composition for crankcase applications
EP2302020A1 (en) 2007-07-28 2011-03-30 Innospec Limited Use of additives for improving oxidation stability of a fuel oil composition
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
US20110105371A1 (en) * 2009-11-05 2011-05-05 Afton Chemical Corporation Olefin copolymer vi improvers and lubricant compositions and uses thereof
US20110118160A1 (en) * 2009-11-18 2011-05-19 Chevron Oronite Company Llc Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals
US20110143979A1 (en) * 2009-12-15 2011-06-16 Chevron Oronite Company Llc Lubricating oil compositions
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
US20110237476A1 (en) * 2010-03-25 2011-09-29 Afton Chemical Corporation Lubricant compositions for improved engine performance
EP2371933A1 (en) 2006-02-06 2011-10-05 The Lubrizol Corporation Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
WO2011143051A1 (en) 2010-05-12 2011-11-17 The Lubrizol Corporation Tartaric acid derivatives in hths fluids
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
WO2011143418A1 (en) 2010-05-12 2011-11-17 Exxonmobil Research And Engineering Company Method for reducing one or more of deposits and friction of a lubricating oil
EP2402421A2 (en) 2010-06-29 2012-01-04 Chevron Oronite Technology B.V. Trunk Piston Engine Lubricating Oil Compositions
WO2012033668A1 (en) 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
WO2012051075A2 (en) 2010-10-12 2012-04-19 Chevron Oronite Company Llc Lubricating composition containing multifunctional borated hydroxylated amine salt of a hindered phenolic acid
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
WO2012084906A1 (en) 2010-12-22 2012-06-28 Rhodia Operations Fuel additive composition containing a dispersion of iron particles and a detergent
WO2012099734A2 (en) 2011-01-21 2012-07-26 Chevron Oronite Company Llc Improved process for preparation of low molecular weight molybdenum succinimide complexes
WO2012099736A2 (en) 2011-01-21 2012-07-26 Chevron Oronite Company Llc Improved process for preparation of high molecular weight molybdenum succinimide complexes
EP2489637A1 (en) 2011-02-17 2012-08-22 Afton Chemical Corporation Cerium oxide nanoparticle additives and lubricant formulations containing the nanoparticle additives
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
EP2524958A1 (en) 2011-05-20 2012-11-21 Afton Chemical Corporation Lubricant compositions containing a heteroaromatic compound
WO2012163935A2 (en) 2011-05-30 2012-12-06 Shell Internationale Research Maatschappij B.V. Liquid fuel compositions
WO2013003394A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyetheramines
WO2013003392A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013003405A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyalkylene glycol mono ethers
WO2013003406A1 (en) 2011-06-29 2013-01-03 Exxonmobil Research And Engineering Company Low viscosity engine oil with superior engine wear protection
WO2013007738A1 (en) 2011-07-12 2013-01-17 Total Raffinage Marketing Additive compositions that improve the stability and the engine performances of diesel fuels
WO2013013026A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Carboxylic pyrrolidinones and methods of use thereof
WO2013012987A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof
EP2557144A1 (en) 2011-08-11 2013-02-13 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
US8377856B2 (en) 2009-05-14 2013-02-19 Afton Chemical Corporation Extended drain diesel lubricant formulations
WO2013043332A1 (en) 2011-09-23 2013-03-28 The Lubrizol Corporation Quaternary ammonium salts in heating oils
WO2013055481A1 (en) 2011-10-10 2013-04-18 Exxonmobil Research And Engineering Company High efficiency engine oil compositions
US8425772B2 (en) 2006-12-12 2013-04-23 Cummins Filtration Ip, Inc. Filtration device with releasable additive
WO2013066915A1 (en) 2011-11-01 2013-05-10 Exxonmobil Research And Engineering Company Lubricants with improved low-temperature fuel economy
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
WO2013074498A1 (en) 2011-11-14 2013-05-23 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013082206A1 (en) 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
EP2604676A1 (en) 2011-12-16 2013-06-19 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
WO2013092533A1 (en) 2011-12-21 2013-06-27 Total Raffinage Marketing Additive compositions that improve the lacquering resistance of superior quality diesel or biodiesel fuels
WO2013096532A1 (en) 2011-12-22 2013-06-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013101256A2 (en) 2011-12-30 2013-07-04 Butamax (Tm) Advanced Biofuels Llc Corrosion inhibitor compositions for oxygenated gasolines
WO2013120985A1 (en) 2012-02-17 2013-08-22 Total Raffinage Marketing Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
WO2013142110A1 (en) 2012-03-22 2013-09-26 Exxonmobil Research And Engineering Company Novel antioxidant combination and synthetic base oils containing the same
WO2013151911A1 (en) 2012-04-04 2013-10-10 The Lubrizol Corporation Bearing lubricants for pulverizing equipment
WO2013165792A1 (en) 2012-05-02 2013-11-07 Lubrizol Advanced Materials, Inc. Aromatic dispersant composition
US8586520B2 (en) 2011-06-30 2013-11-19 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013181318A1 (en) 2012-06-01 2013-12-05 Exxonmobil Research And Engineering Company Lubricant compostions and processes for preparing same
WO2013182581A1 (en) 2012-06-06 2013-12-12 Evonik Oil Additives Gmbh Fuel efficient lubricating oils
WO2014008121A1 (en) 2012-07-02 2014-01-09 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
US8632638B2 (en) 2010-11-19 2014-01-21 Chevron Oronite Company Llc Method for cleaning deposits from an engine fuel delivery system
EP2687582A1 (en) 2012-07-18 2014-01-22 Afton Chemical Corporation Lubricant compositions for direct injection engines
US8702968B2 (en) 2011-04-05 2014-04-22 Chevron Oronite Technology B.V. Low viscosity marine cylinder lubricating oil compositions
US8703680B2 (en) 2010-11-24 2014-04-22 Chevron Oronite Company Llc Lubricating composition containing friction modifier blend
WO2014066444A1 (en) 2012-10-24 2014-05-01 Exxonmobil Research And Engineering Comapny Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
WO2014066344A1 (en) 2012-10-23 2014-05-01 The Lubrizol Corporation Diesel detergent without a low molecular weight penalty
WO2014065984A1 (en) 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
US8716202B2 (en) 2010-12-14 2014-05-06 Chevron Oronite Company Llc Method for improving fluorocarbon elastomer seal compatibility
EP2727984A1 (en) 2012-11-02 2014-05-07 Infineum International Limited Marine engine lubrication
EP2735603A1 (en) 2012-11-21 2014-05-28 Infineum International Limited Marine engine lubrication
WO2014088814A1 (en) 2012-12-07 2014-06-12 The Lubrizol Corporation Pyran dispersants
WO2014107315A1 (en) 2013-01-04 2014-07-10 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2014107314A1 (en) 2013-01-03 2014-07-10 Exxonmobil Research And Engineering Company Lubricating compositions having improved shear stability
US8796192B2 (en) 2010-10-29 2014-08-05 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
EP2765179A1 (en) 2013-02-07 2014-08-13 Infineum International Limited Marine engine lubrication
US20140262950A1 (en) * 2013-03-14 2014-09-18 Exxonmobil Research And Engineering Company Hydrohalogenation of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US8841243B2 (en) 2010-03-31 2014-09-23 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
WO2014149406A1 (en) 2013-03-15 2014-09-25 Exxonmobil Research And Engineering Company Method for improving thermal -oxidative stability and elastomer compatibility
WO2014158533A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Lubricating composition providing high wear resistance
WO2014158602A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Method for improving emulsion characteristics of engine oils
WO2014193692A1 (en) 2013-05-28 2014-12-04 The Lubrizol Corporation Asphaltene inhibition
US8933002B2 (en) 2011-11-10 2015-01-13 Chevron Oronite Company Llc Lubricating oil compositions
US8969273B2 (en) 2009-02-18 2015-03-03 Chevron Oronite Company Llc Lubricating oil compositions
WO2015031043A1 (en) 2013-08-29 2015-03-05 Lubrizol Advanced Materials, Inc. Non-fused aromatic dispersant composition
EP2851412A1 (en) 2013-09-24 2015-03-25 Infineum International Limited Marine engine lubrication
WO2015048011A1 (en) 2013-09-25 2015-04-02 3M Innovative Properties Company Multi-layered polishing pads
WO2015047939A1 (en) 2013-09-25 2015-04-02 3M Innovative Properties Company Composite ceramic abrasive polishing solution
WO2015050690A1 (en) 2013-10-03 2015-04-09 Exxonmobil Research And Engineering Company Compositions with improved varnish control properties
WO2015088893A1 (en) 2013-12-10 2015-06-18 The Lubrizol Corporation Organic salts of glyceride-cyclic carboxylic acid anhydride adducts as corrosion inhibitors
US9062271B2 (en) 2013-10-30 2015-06-23 Chevron Oronite Technology B.V. Process for preparing an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition
US9062273B2 (en) 2009-12-15 2015-06-23 Chevron Oronite Company Llc Lubricating oil compositions containing titanium complexes
WO2015095336A1 (en) 2013-12-18 2015-06-25 Chevron Phillips Chemical Company Lp Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins
WO2015099907A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Low viscosity ester lubricant and method for using
WO2015099821A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099820A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099819A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015113681A1 (en) 2014-01-29 2015-08-06 Basf Se Polycarboxylic-acid-based additives for fuels and lubricants
US9150472B2 (en) 2011-12-21 2015-10-06 Shell Oil Company Method and composition for inhibiting asphaltene deposition in a hydrocarbon mixture
WO2015157071A1 (en) 2014-04-08 2015-10-15 Lubrizol Advanced Materials, Inc. Ink jet ink compositions
EP2940110A1 (en) 2014-04-29 2015-11-04 Infineum International Limited Lubricating oil compositions
WO2015171980A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171292A1 (en) 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
WO2015171978A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171981A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015183455A1 (en) 2014-05-29 2015-12-03 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2015200592A1 (en) 2014-06-27 2015-12-30 The Lubrizol Corporation Mixtures of friction modifiers to provide good friction performance to transmission fluids
US9249091B2 (en) 2011-12-27 2016-02-02 Chevron Oronite Company Llc Post-treated sulfurized salt of an alkyl-substituted hydroxyaromatic composition
WO2016043944A1 (en) 2014-09-17 2016-03-24 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9315756B2 (en) 2012-04-06 2016-04-19 Exxonmobil Research And Engineering Company Bio-feeds based hybrid group V base stocks and method of production thereof
US9334460B2 (en) 2013-03-14 2016-05-10 Exxonmobil Research And Engineering Company Ring opening cross metathesis of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
WO2016073149A1 (en) 2014-11-03 2016-05-12 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
EP3020790A1 (en) 2014-11-14 2016-05-18 Chevron Oronite Technology B.V. Trunk piston engine oil composition for low sulfur marine distillate fueled engines
WO2016077134A1 (en) 2014-11-12 2016-05-19 The Lubrizol Corporation Mixed phosphorus esters for lubricant applications
EP3029133A1 (en) 2014-12-04 2016-06-08 Infineum International Limited Marine engine lubrication
WO2016106214A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for determining condition and quality of petroleum products
WO2016106211A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for authentication and identification of petroleum products
WO2016109382A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2016109322A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109376A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US9416307B2 (en) 2011-12-21 2016-08-16 Shell Oil Company Method and composition for inhibiting wax in a hydrocarbon mixture
US9422497B2 (en) 2012-09-21 2016-08-23 Exxonmobil Research And Engineering Company Synthetic lubricant basestocks and methods of preparation thereof
US9434906B2 (en) 2013-03-25 2016-09-06 Chevron Oronite Company, Llc Marine diesel engine lubricating oil compositions
WO2016144639A1 (en) 2015-03-10 2016-09-15 The Lubrizol Corporation Lubricating compositions comprising an anti-wear/friction modifying agent
US9453173B2 (en) 2011-12-21 2016-09-27 Shell Oil Company Method and composition for inhibiting foam in a hydrocarbon mixture
US9506008B2 (en) 2013-12-23 2016-11-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2016191409A1 (en) 2015-05-28 2016-12-01 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016200606A1 (en) 2015-06-09 2016-12-15 Exxonmobil Research And Engineering Company Inverse micellar compositions containing lubricant additives
US9528071B2 (en) 2015-02-13 2016-12-27 Chevron Oronite Technology B.V. Lubricating oil compositions with enhanced piston cleanliness
US9528074B2 (en) 2015-02-13 2016-12-27 Chevron Oronite Technology B.V. Lubricating oil compositions with enhanced piston cleanliness
WO2017007670A1 (en) 2015-07-07 2017-01-12 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
EP3135750A1 (en) 2015-08-26 2017-03-01 Infineum International Limited Lubricating oil compositions
US9617482B2 (en) 2013-03-14 2017-04-11 Exxonmobil Research And Engineering Company Functionalized polymers containing polyamine succinimide for demulsification in hydrocarbon refining processes
WO2017083042A1 (en) 2015-11-09 2017-05-18 The Lubrizol Corporation Using quaternary amine additives to improve water separation
US9663727B2 (en) 2013-03-14 2017-05-30 Exxonmobil Research And Engineering Company Functionalized polymers containing polyamine succinimide for antifouling in hydrocarbon refining processes
WO2017117178A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
US9732300B2 (en) 2015-07-23 2017-08-15 Chevron Phillipa Chemical Company LP Liquid propylene oligomers and methods of making same
EP3205705A1 (en) 2013-06-07 2017-08-16 Basf Se Alkylene oxide and hydrocarbyl-substituted polycarboxylic acid quaternised alkylamine as additives in fuels and lubricants and their use
WO2017142805A1 (en) 2016-02-16 2017-08-24 3M Innovative Properties Company Polishing systems and methods of making and using same
WO2017146897A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017146896A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017172254A1 (en) 2016-03-31 2017-10-05 Exxonmobil Research And Engineering Company Lubricant compositions
EP3246383A1 (en) 2016-05-17 2017-11-22 Afton Chemical Corporation Synergistic dispersants
WO2017200688A1 (en) 2016-05-18 2017-11-23 The Lubrizol Corporation Hydraulic fluid composition
WO2017205274A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205271A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205270A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017218664A1 (en) 2016-06-17 2017-12-21 The Lubrizol Corporation Lubricating compositions
WO2018013249A1 (en) 2016-07-12 2018-01-18 Chevron Phillips Chemical Company Lp Decene oligomers
WO2018017449A1 (en) 2016-07-20 2018-01-25 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants
WO2018017454A1 (en) 2016-07-20 2018-01-25 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants
US9879202B2 (en) 2014-12-04 2018-01-30 Infineum International Limited Marine engine lubrication
US9885004B2 (en) 2013-12-23 2018-02-06 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2018026982A1 (en) 2016-08-03 2018-02-08 Exxonmobil Research And Engineering Company Lubricating engine oil for improved wear protection and fuel efficiency
WO2018027227A1 (en) 2016-08-05 2018-02-08 Rutgers, The State University Of New Jersey Thermocleavable friction modifiers and methods thereof
US9909079B2 (en) 2013-10-18 2018-03-06 Chevron Oronite Company Llc Lubricating oil composition for protection of silver bearings in medium speed diesel engines
US9926509B2 (en) 2015-01-19 2018-03-27 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection and solubility
WO2018057678A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
WO2018057377A1 (en) 2016-09-20 2018-03-29 Exxonmobil Research And Engineering Company Non-newtonian engine oil with superior engine wear protection and fuel economy
WO2018057675A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Polyacrylate antifoam components with improved thermal stability
WO2018067906A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company High conductivity lubricating oils for electric and hybrid vehicles
WO2018067903A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains
WO2018067905A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains
EP3336163A1 (en) 2016-12-13 2018-06-20 Afton Chemical Corporation Polyolefin-derived dispersants
EP3339404A1 (en) 2006-07-18 2018-06-27 Infineum International Limited Lubricating oil compositions
WO2018118163A1 (en) 2016-12-22 2018-06-28 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
WO2018118477A1 (en) 2016-12-19 2018-06-28 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition compression spark ignition engines
WO2018125956A1 (en) 2016-12-30 2018-07-05 Exxonmobil Research And Engineering Company Low viscosity lubricating oil compositions for turbomachines
WO2018144167A1 (en) 2017-02-01 2018-08-09 Exxonmobil Research And Engineering Company Lubricating engine oil and method for improving engine fuel efficiency
WO2018156304A1 (en) 2017-02-21 2018-08-30 Exxonmobil Research And Engineering Company Lubricating oil compositions and methods of use thereof
EP3369802A1 (en) 2017-03-01 2018-09-05 Infineum International Limited Improvements in and relating to lubricating compositions
WO2018170110A1 (en) 2017-03-16 2018-09-20 Chevron Phillips Chemical Company Lp Lubricant compositions containing hexene-based oligomers
WO2018175830A1 (en) 2017-03-24 2018-09-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency and energy efficiency
WO2018197312A1 (en) 2017-04-27 2018-11-01 Shell Internationale Research Maatschappij B.V. Lubricating composition
US10138438B2 (en) 2015-02-18 2018-11-27 Chevron Oronite Technology B.V. Low sulfur marine distillate fuel trunk piston engine oil composition
WO2018236592A1 (en) 2017-06-20 2018-12-27 The Lubrizol Corporation Lubricating composition
EP3421576A1 (en) 2017-06-30 2019-01-02 Infineum International Limited Refinery antifoulant process
US10174272B2 (en) 2016-07-14 2019-01-08 Afton Chemical Corporation Dispersant viscosity index improver-containing lubricant compositions and methods of use thereof
WO2019014092A1 (en) 2017-07-13 2019-01-17 Exxonmobil Research And Engineering Company Continuous process for the manufacture of grease
WO2019018145A1 (en) 2017-07-21 2019-01-24 Exxonmobil Research And Engineering Company Method for improving deposit control and cleanliness performance in an engine lubricated with a lubricating oil
US10190072B2 (en) 2013-12-23 2019-01-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2019028310A1 (en) 2017-08-04 2019-02-07 Exxonmobil Research And Engineering Company Novel formulation for lubrication of hyper compressors providing improved pumpability under high-pressure conditions
WO2019055291A1 (en) 2017-09-18 2019-03-21 Exxonmobil Research And Engineering Company Hydraulic oil compositions with improved hydrolytic and thermo-oxidative stability
WO2019060144A1 (en) 2017-09-22 2019-03-28 Exxonmobil Research And Engineering Company Lubricating oil compositions with viscosity and deposit control
EP3461877A1 (en) 2017-09-27 2019-04-03 Infineum International Limited Improvements in and relating to lubricating compositions
WO2019089177A1 (en) 2017-10-30 2019-05-09 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2019090038A1 (en) 2017-11-03 2019-05-09 Exxonmobil Research And Engineering Company Lubricant compositions with improved performance and methods of preparing and using the same
EP3483234A1 (en) 2013-09-20 2019-05-15 Basf Se Use of specialised derivatives of quaternised nitrogen compounds as additives in fuels and lubricants
WO2019094019A1 (en) 2017-11-09 2019-05-16 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness
WO2019103808A1 (en) 2017-11-22 2019-05-31 Exxonmobil Research And Engineering Company Lubricating oil compositions with oxidative stability in diesel engines
US10316712B2 (en) 2015-12-18 2019-06-11 Exxonmobil Research And Engineering Company Lubricant compositions for surface finishing of materials
EP3495462A1 (en) 2017-12-11 2019-06-12 Infineum International Limited Low ash and ash-free acid neutralizing compositions and lubricating oil compositions containing same
WO2019112711A1 (en) 2017-12-04 2019-06-13 Exxonmobil Research And Enginerring Company Method for preventing or reducing low speed pre-ignition
WO2019118115A1 (en) 2017-12-15 2019-06-20 Exxonmobil Research And Engineering Company Lubricating oil compositions containing microencapsulated additives
WO2019133409A1 (en) 2017-12-28 2019-07-04 Exxonmobil Research And Engineering Company Friction and wear reduction using liquid crystal base stocks
WO2019133218A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Lubricating oil compositions with wear and sludge control
WO2019133191A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Lubrication of oxygenated diamond-like carbon surfaces
WO2019133255A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Grease compositions with improved performance comprising thixotropic polyamide, and methods of preparing and using the same
US10351791B2 (en) 2013-07-26 2019-07-16 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
US10364403B2 (en) 2013-11-06 2019-07-30 Chevron Oronite Technology B.V. Marine diesel cylinder lubricant oil compositions
US10364404B2 (en) 2014-12-04 2019-07-30 Infineum International Limited Marine engine lubrication
WO2019183365A1 (en) 2018-03-21 2019-09-26 The Lubrizol Corporation NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids
US10435491B2 (en) 2015-08-19 2019-10-08 Chevron Phillips Chemical Company Lp Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins
US10450525B2 (en) 2014-08-27 2019-10-22 Chevron Oronite Company Llc Process for alaknolamide synthesis
WO2019217058A1 (en) 2018-05-11 2019-11-14 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US10494579B2 (en) 2016-04-26 2019-12-03 Exxonmobil Research And Engineering Company Naphthene-containing distillate stream compositions and uses thereof
WO2019240965A1 (en) 2018-06-11 2019-12-19 Exxonmobil Research And Engineering Company Non-zinc-based antiwear compositions, hydraulic oil compositions, and methods of using the same
US10519394B2 (en) 2014-05-09 2019-12-31 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness
EP3597726A1 (en) 2018-07-20 2020-01-22 Afton Chemical Corporation Fuel-soluble synergistic cleaning mixture for high pressure gasoline engines
WO2020023437A1 (en) 2018-07-24 2020-01-30 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine corrosion protection
WO2020023430A1 (en) 2018-07-23 2020-01-30 Exxonmobil Research And Engineering Company Lubricating oil compositions with oxidative stability in diesel engines using biodiesel fuel
US10550335B2 (en) 2015-12-28 2020-02-04 Exxonmobil Research And Engineering Company Fluxed deasphalter rock fuel oil blend component oils
US10550341B2 (en) 2015-12-28 2020-02-04 Exxonmobil Research And Engineering Company Sequential deasphalting for base stock production
US10556316B2 (en) 2015-05-13 2020-02-11 3M Innovative Properties Company Polishing pads and systems for and methods of using same
WO2020068439A1 (en) 2018-09-27 2020-04-02 Exxonmobil Research And Engineering Company Low viscosity lubricating oils with improved oxidative stability and traction performance
US10647936B2 (en) 2016-12-30 2020-05-12 Exxonmobil Research And Engineering Company Method for improving lubricant antifoaming performance and filterability
WO2020096804A1 (en) 2018-11-05 2020-05-14 Exxonmobil Research And Engineering Company Lubricating oil compositions having improved cleanliness and wear performance
US10669506B2 (en) 2013-11-06 2020-06-02 Chevron Oronite Technology B.V. Marine diesel cylinder lubricant oil compositions
WO2020112338A1 (en) 2018-11-28 2020-06-04 Exxonmobil Research And Engineering Company Lubricating oil compositions with improved deposit resistance and methods thereof
WO2020123440A1 (en) 2018-12-10 2020-06-18 Exxonmobil Research And Engineering Company Method for improving oxidation and deposit resistance of lubricating oils
US10689589B2 (en) 2015-07-28 2020-06-23 Innospec Limited Cyclic quaternary ammonium salts as fuel or lubricant additives
US10689593B2 (en) 2014-08-15 2020-06-23 Exxonmobil Research And Engineering Company Low viscosity lubricating oil compositions for turbomachines
WO2020131515A2 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricant compositions with improved wear control
WO2020131441A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having improved performance
WO2020131310A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Method for improving high temperature antifoaming performance of a lubricating oil
WO2020131439A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having polyurea thickeners made with isocyanate terminated prepolymers
WO2020132164A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricating oil compositions with viscosity control
WO2020132166A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricating oil compositions with antioxidant formation and dissipation control
WO2020131440A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having calcium sulfonate and polyurea thickeners
WO2020139333A1 (en) 2018-12-26 2020-07-02 Exxonmobil Research And Engineering Company Formulation approach to extend the high temperature performance of lithium complex greases
US10712105B1 (en) 2019-06-19 2020-07-14 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
EP3680312A1 (en) 2019-01-11 2020-07-15 Afton Chemical Corporation Oxazoline modified dispersants
WO2020149958A1 (en) 2019-01-18 2020-07-23 Afton Chemical Corporation Engine oils for soot handling and friction reduction
WO2020150123A1 (en) 2019-01-17 2020-07-23 The Lubrizol Corporation Traction fluids
EP3690009A1 (en) 2019-01-31 2020-08-05 Afton Chemical Corporation Fuel additive mixture providing rapid injector clean-up in high pressure gasoline engines
WO2020176171A1 (en) 2019-02-28 2020-09-03 Exxonmobil Research And Engineering Company Low viscosity gear oil compositions for electric and hybrid vehicles
US10774722B2 (en) 2018-09-04 2020-09-15 Afton Chemical Corporation Predictive methods for emissions control systems performance
US10774708B2 (en) 2018-09-04 2020-09-15 Afton Chemical Corporation Gasoline particulate filters with high initial filtering efficiency and methods of making same
US10781397B2 (en) 2014-12-30 2020-09-22 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US10793801B2 (en) 2017-02-06 2020-10-06 Exxonmobil Chemical Patents Inc. Low transition temperature mixtures and lubricating oils containing the same
US10808196B2 (en) 2017-03-28 2020-10-20 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity reducing base stocks and lubricating oil formulations containing the same
EP3739025A1 (en) 2019-05-13 2020-11-18 Afton Chemical Corporation Additive and lubricant for industrial lubrication
US10858610B2 (en) 2017-03-24 2020-12-08 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
WO2020257376A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257370A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257379A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257371A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257374A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257373A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257375A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257378A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257377A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
US10876062B2 (en) 2017-03-24 2020-12-29 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
WO2020264534A2 (en) 2019-06-27 2020-12-30 Exxonmobil Research And Engineering Company Method for reducing solubilized copper levels in wind turbine gear oils
EP3760696A1 (en) 2018-12-20 2021-01-06 Infineum International Limited Oil anti-foulant and/or asphaltene agglomeration process
EP3778841A1 (en) 2019-08-15 2021-02-17 Infineum International Limited Method for reducing piston deposits in a marine diesel engine
WO2021090020A1 (en) 2019-11-08 2021-05-14 Innospec Limited Compositions and methods and uses relating thereto
WO2021090021A1 (en) 2019-11-08 2021-05-14 Innospec Limited Compositions, and methods and uses relating thereto
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
EP3825387A1 (en) 2019-11-22 2021-05-26 Afton Chemical Corporation Fuel-soluble cavitation inhibitor for fuels used in common-rail injection engines
EP3835392A1 (en) 2018-12-20 2021-06-16 Infineum International Limited Hydrocarbon marine fuel oil
WO2021138285A1 (en) 2020-01-03 2021-07-08 Afton Chemical Corporation Silicone functionlized viscosity index improver
US11078418B2 (en) 2016-07-05 2021-08-03 Basf Se Corrosion inhibitors for fuels and lubricants
WO2021154497A1 (en) 2020-01-30 2021-08-05 Exxonmobil Research And Engineering Company Sulfur-free, ashless, low phosphorus lubricant compositions with improved oxidation stability
WO2021183230A1 (en) 2020-03-12 2021-09-16 The Lubrizol Corporation Oil-based corrosion inhibitors
WO2021194813A1 (en) 2020-03-27 2021-09-30 Exxonmobil Research And Engineering Company Monitoring health of heat transfer fluids for electric systems
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use
WO2022010606A1 (en) 2020-07-09 2022-01-13 Exxonmobil Research And Engineering Company Engine oil lubricant compositions and methods for making same with superior engine wear protection and corrosion protection
WO2022009105A1 (en) 2020-07-07 2022-01-13 Chevron Oronite Company Llc Fuel additives for mitigating injector nozzle fouling and reducing particulate emissions
WO2022058894A1 (en) 2020-09-17 2022-03-24 Chevron Oronite Company Llc Aryloxy alkylamines as fuel additives for reducing injector fouling in direct injection spark ignition gasoline engines
WO2022072962A1 (en) 2020-09-30 2022-04-07 Exxonmobil Research And Engineering Company Low friction and low traction lubricant compositions useful in dry clutch motorcycles
WO2022099291A1 (en) 2020-11-06 2022-05-12 Exxonmobil Research And Engineering Company Engine oil lubricant compositions and methods for making same with steel corrosion protection
EP4079828A1 (en) 2018-03-29 2022-10-26 Innospec Limited Composition, method and use
EP4105301A1 (en) 2021-06-15 2022-12-21 Basf Se New gasoline additive packages
WO2023057943A1 (en) 2021-10-06 2023-04-13 Chevron Oronite Company Llc Fuel additives for lowering deposit and particulate emission
US11639480B1 (en) 2022-06-20 2023-05-02 Afton Chemical Corporation Phosphorus antiwear system for improved gear protection
EP4180505A1 (en) 2021-11-15 2023-05-17 Infineum International Limited Improvements in marine fuels
WO2023111550A1 (en) 2021-12-14 2023-06-22 Innospec Limited Methods and uses relating to fuel compositions
WO2023122405A1 (en) 2021-12-21 2023-06-29 ExxonMobil Technology and Engineering Company Engine oil lubricant compostions and methods for making same with superior oil consumption
EP4212604A1 (en) 2022-01-13 2023-07-19 TotalEnergies One Tech Stabilised compositions comprising olefins
US11760952B2 (en) 2021-01-12 2023-09-19 Ingevity South Carolina, Llc Lubricant thickener systems from modified tall oil fatty acids, lubricating compositions, and associated methods
EP4282937A1 (en) 2022-05-26 2023-11-29 Afton Chemical Corporation Engine oil formluation for controlling particulate emissions
WO2023247973A1 (en) 2022-06-24 2023-12-28 Innospec Limited Fuel compositions comprising an additive, and methods and uses relating thereto
WO2024006132A1 (en) 2022-06-27 2024-01-04 The Lubrizol Corporation Lubricating composition
US11884893B1 (en) 2023-03-31 2024-01-30 Afton Chemical Corporation Antiwear system for improved copper corrosion
US11884892B1 (en) 2023-03-31 2024-01-30 Afton Chemical Corporation Antiwear system for improved copper corrosion
EP4342964A1 (en) 2022-09-22 2024-03-27 Afton Chemical Corporation Extreme pressure additives with improved copper corrosion
US11958875B1 (en) 2023-03-31 2024-04-16 Afton Chemical Corporation Thiophosphoric acid products for antiwear additives
EP4353804A1 (en) 2022-10-11 2024-04-17 Infineum International Limited Functionalized c4 to c5 olefin polymers and lubricant compositions containing such
EP4353805A1 (en) 2022-10-11 2024-04-17 Infineum International Limited Lubricant composition containing metal alkanoate
EP4357443A1 (en) 2022-10-18 2024-04-24 Infineum International Limited Lubricating oil compositions
WO2024086192A1 (en) 2022-10-18 2024-04-25 The Lubrizol Corporation Hydraulic fluid composition
EP4368687A1 (en) 2022-11-10 2024-05-15 Afton Chemical Corporation Corrosion inhibitor and industrial lubricant including the same
EP4386070A1 (en) 2022-12-09 2024-06-19 Afton Chemical Corporation Driveline and transmission fluids for low speed wear and scuffing
WO2024126998A1 (en) 2022-12-12 2024-06-20 Innospec Limited Composition, method and use
EP4397738A1 (en) 2023-01-03 2024-07-10 Infineum International Limited Method for reduction of abnormal combustion events
US12054688B1 (en) 2023-03-31 2024-08-06 Afton Chemical Corporation Antiwear system for improved copper corrosion
EP4428212A1 (en) 2023-03-10 2024-09-11 Infineum International Limited Asphaltene deposition control
WO2024206634A1 (en) 2023-03-29 2024-10-03 Chevron Oronite Company Llc Fuel additive compositions and methods for controlling carbon deposits in an internal combustion engines
EP4442797A1 (en) 2023-03-03 2024-10-09 Afton Chemical Corporation Lubricating composition for gear fluids

Families Citing this family (128)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1309907A (en) * 1969-06-30 1973-03-14 Shell Int Research Fuel composition
NL169595C (en) * 1970-05-21 1982-08-02 Shell Int Research PROCESS FOR PREPARING AMINS AND LUBRICATING OILS AND LIQUID ENGINE FUELS CONTAINING THESE.
US3717446A (en) * 1970-12-31 1973-02-20 Union Oil Co Gasoline anti-icing additives (a)
NL176177C (en) * 1971-09-21 1985-03-01 Shell Int Research PROCESS FOR THE PREPARATION OF AMINES SUITABLE AS ADDITIVE FOR LUBRICANTS AND FUELS.
GB1338618A (en) * 1971-11-16 1973-11-28 Shell Int Research Gasoline compositions
US3767574A (en) * 1971-12-06 1973-10-23 Phillips Petroleum Co Gasoline additive
US3907518A (en) * 1972-08-11 1975-09-23 Rohm & Haas Detergent motor fuel
US3909428A (en) * 1972-10-11 1975-09-30 Atlantic Richfield Co Composition and method
GB1405305A (en) * 1972-11-29 1975-09-10 British Petroleum Co Gasoline composition
US3852258A (en) * 1972-12-18 1974-12-03 Chevron Res Process for preparing polyolefin substituted amines
US3898056A (en) * 1972-12-26 1975-08-05 Chevron Res Hydrocarbylamine additives for distillate fuels
US3876704A (en) * 1973-08-09 1975-04-08 Union Oil Co Detergent automotive fuel composition
US3884647A (en) * 1973-08-09 1975-05-20 Union Oil Co Detergent automotive fuel composition
US4065499A (en) * 1973-09-07 1977-12-27 Ethyl Corporation Lubricant additive
US3912641A (en) * 1973-09-27 1975-10-14 Lubrizol Corp Sulfur and nitrogen-containing organic compositions processes for making them and fuels and additives containing them
US3960515A (en) * 1973-10-11 1976-06-01 Chevron Research Company Hydrocarbyl amine additives for distillate fuels
US4330302A (en) * 1973-11-21 1982-05-18 Exxon Research & Engineering Co. High thermal stability liquid hydrocarbons and methods for producing them
US3864098A (en) * 1974-01-07 1975-02-04 Chevron Res Fuel additives
US4105417A (en) * 1974-04-11 1978-08-08 Coon Marvin D Fuel additive
US4039300A (en) * 1974-06-03 1977-08-02 Atlantic Richfield Company Gasoline fuel composition and method of using
US4128403A (en) * 1974-09-06 1978-12-05 Chevron Research Company Fuel additive for distillate fuels
DE2555920C2 (en) * 1974-12-24 1983-12-15 Rohm and Haas Co., 19105 Philadelphia, Pa. Multipurpose additive for gasoline and a fuel mixture containing it
DE2555922C2 (en) * 1974-12-24 1984-09-20 Rohm And Haas Co., Philadelphia, Pa. Multipurpose additive mixture for gasoline
US4068057A (en) * 1975-03-05 1978-01-10 Exxon Research And Engineering Company Aminated polymeric additives for fuel and lubricants
US4082518A (en) * 1975-04-28 1978-04-04 Phillips Petroleum Company Additives for motor fuels and lubricants
US4191537A (en) * 1976-06-21 1980-03-04 Chevron Research Company Fuel compositions of poly(oxyalkylene) aminocarbamate
US4160648A (en) * 1976-06-21 1979-07-10 Chevron Research Company Fuel compositions containing deposit control additives
US4288612A (en) * 1976-06-21 1981-09-08 Chevron Research Company Deposit control additives
US4236020A (en) * 1976-06-21 1980-11-25 Chevron Research Company Carbamate deposit control additives
US4166726A (en) * 1977-12-16 1979-09-04 Chevron Research Company Diesel fuel containing polyalkylene amine and Mannich base
US4233168A (en) * 1978-06-19 1980-11-11 Chevron Research Company Lubricant compositions containing dispersant additives
US4362633A (en) * 1980-10-10 1982-12-07 Standard Oil Company (Indiana) Molybdenum-containing aminated sulfurized olefin lubricating oil additives
DE3611230A1 (en) * 1986-04-04 1987-10-08 Basf Ag POLYBUTYL AND POLYISOBUTYLAMINE, METHOD FOR THE PRODUCTION THEREOF AND THE FUEL AND LUBRICANT COMPOSITIONS CONTAINING THE SAME
DE3700363A1 (en) * 1987-01-08 1988-07-21 Basf Ag FUEL OR LUBRICANT COMPOSITION AND USE OF POLYBUTYL OR POLYISOBUTYL DERIVATIVES IN THE SAME
US4863487A (en) * 1987-04-29 1989-09-05 Nalco Chemical Company Hydrocarbon fuel detergent
US4895578A (en) * 1987-04-29 1990-01-23 Nalco Chemical Company Hydrocarbon fuel detergent
US4852993A (en) * 1987-08-12 1989-08-01 Texaco Inc. ORI-inhibited and deposit-resistant motor fuel composition
CA1329481C (en) * 1988-02-04 1994-05-17 Rodney Lu-Dai Sung Ori-inhibited motor fuel composition and storage stable concentrate
US5055607A (en) * 1988-09-09 1991-10-08 Chevron Research Company Long chain aliphatic hydrocarbyl amine additives having an oxy-carbonyl connecting group
US4865621A (en) * 1989-01-27 1989-09-12 Texaco Inc. Ori-inhibited and deposit-resistant motor fuel composition
US4968321A (en) * 1989-02-06 1990-11-06 Texaco Inc. ORI-inhibited motor fuel composition
WO1990010051A1 (en) * 1989-02-21 1990-09-07 Union Oil Company Of California Fuel composition for control of intake valve deposits
US5006130A (en) * 1989-06-28 1991-04-09 Shell Oil Company Gasoline composition for reducing intake valve deposits in port fuel injected engines
US6034184A (en) * 1998-06-23 2000-03-07 Mobil Oil Corporation Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: Mannich reaction products
US6103676A (en) * 1998-06-23 2000-08-15 Mobil Oil Corporation Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: hydroformylation/reductive amination reaction products
US6248702B1 (en) 1990-01-16 2001-06-19 Mobil Oil Corporation Dispersant and dispersant viscosity index improvers from selectively hydrogenated aryl-substituted olefin containing diene copolymers
US6054539A (en) * 1998-07-31 2000-04-25 Mobil Oil Corporation Selectively hydrogenated polymer compositions: polybutadiene-isoprene-polybutadiene
US6162768A (en) * 1990-01-16 2000-12-19 Mobil Oil Corporation Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: free radically initiated direct grafting reaction products
US6228817B1 (en) 1990-01-16 2001-05-08 Mobil Oil Corporation Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers
GB9003023D0 (en) * 1990-02-09 1990-04-04 Exxon Chemical Patents Inc Gasoline fuel for internal combustion engines
US6488723B2 (en) 1990-03-05 2002-12-03 Alfred Richard Nelson Motor fuel additive composition and method for preparation thereof
ES2081472T3 (en) * 1990-03-05 1996-03-16 Polar Molecular Corp COMPOSITION OF ADDITIVE FOR ENGINE FUELS AND METHOD FOR ITS PREPARATION.
US5242469A (en) * 1990-06-07 1993-09-07 Tonen Corporation Gasoline additive composition
DE4035609A1 (en) * 1990-11-09 1992-05-14 Basf Ag FUELS FOR OTTO ENGINES
US5248315A (en) * 1990-11-15 1993-09-28 Euron S.P.A. Detergent additive for fuels
US5211721A (en) * 1991-02-25 1993-05-18 Texaco Inc. Polyoxyalkylene ester compounds and ORI-inhibited motor fuel compositions
US5462567A (en) * 1992-12-28 1995-10-31 Chevron Chemical Company Fuel additive compositions containing poly(oxyalkylene)hydroxyaromatic esters and aliphatic amines
US5516342A (en) * 1992-12-28 1996-05-14 Chevron Chemical Company Fuel additive compositions containing poly(oxyalkylene) hydroxyaromatic ethers and aliphatic amines
US5755835A (en) * 1992-12-28 1998-05-26 Chevron Chemical Company Fuel additive compositions containing aliphatic amines and polyalkyl hydroxyaromatics
US5352251A (en) * 1993-03-30 1994-10-04 Shell Oil Company Fuel compositions
US5691422A (en) * 1994-03-07 1997-11-25 Exxon Chemical Patents Inc. Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof
US5674950A (en) * 1994-03-07 1997-10-07 Exxon Chemical Patents Inc. Polymers having terminal hydroxyl aldehyde, or alkylamino substitutents and derivatives thereof
DE4412489A1 (en) * 1994-04-12 1995-10-19 Basf Ag Fuel or lubricant additives, processes for their preparation and fuel or lubricant compositions containing these additives
US5405419A (en) * 1994-05-02 1995-04-11 Chevron Chemical Company Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool
US5405418A (en) * 1994-05-02 1995-04-11 Chevron Chemical Company Fuel additive compositions containing an aliphatic amine, a polyolefin and an aromatic ester
US5458661A (en) * 1994-09-19 1995-10-17 Shell Oil Company Fuel compositions
US5855630A (en) * 1994-09-19 1999-01-05 Shell Oil Company Fuel compositions
US5458660A (en) * 1994-09-19 1995-10-17 Shell Oil Company Fuel compositions
US5489315A (en) * 1994-09-19 1996-02-06 Shell Oil Company Fuel compositions comprising hydantoin-containing polyether alcohol additives
US5507843A (en) * 1994-09-19 1996-04-16 Shell Oil Company Fuel compositions
US6312481B1 (en) 1994-09-22 2001-11-06 Shell Oil Company Fuel compositions
IT1270656B (en) 1994-10-13 1997-05-07 Euron Spa FUEL COMPOSITION
US5789356A (en) * 1994-10-13 1998-08-04 Exxon Chemical Patents Inc Synergistic combinations for use in functional fluid compositions
US5559270A (en) * 1994-12-15 1996-09-24 Petrokleen, Ltd. Method of synthesizing pure additives and the improved compositions thereby produced
US5962738A (en) * 1994-12-15 1999-10-05 Petrokleen, Ltd. Polymeric-amine fuel and lubricant additive
US5858929A (en) * 1995-06-09 1999-01-12 The Lubrizol Corporation Composition for providing anti-shudder friction durability performance for automatic transmissions
DE19525938A1 (en) * 1995-07-17 1997-01-23 Basf Ag Process for the production of organic nitrogen compounds, special organic nitrogen compounds and mixtures of such compounds and their use as fuel and lubricant additives
DE19548145A1 (en) * 1995-12-21 1997-06-26 Basf Ag Fuel or lubricant compositions containing secondary polyisobutenamines
AU4355997A (en) * 1996-09-23 1998-04-14 Petrokleen, Ltd. Method of synthesizing pure additives and the improved compositions thereby produced
US5755832A (en) * 1996-11-07 1998-05-26 Chevron Chemical Company Fuel additive concentrate containing tagging material
US5752989A (en) * 1996-11-21 1998-05-19 Ethyl Corporation Diesel fuel and dispersant compositions and methods for making and using same
US6261327B1 (en) 1997-05-29 2001-07-17 Shell Oil Company Additive concentrates for rapidly reducing octane requirement
US5993499A (en) * 1997-06-27 1999-11-30 Chevron Chemical Company Fuel composition containing an aliphatic amine and a poly (oxyalkylene) monool
KR100284175B1 (en) * 1997-12-31 2001-05-02 이정국 Polyalkenyl amine compound substituted with a plurality of hydroxyl groups and fuel oil composition containing the same
US6319881B1 (en) 1998-06-23 2001-11-20 Exxonmobil Oil Corporation Haze free oil additive compositions containing dispersants from selectively hydrogenated diene copolymers
US6215033B1 (en) 1998-12-11 2001-04-10 Mobil Oil Corporation Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: blends with lower molecular weight components
EP1122295A4 (en) * 1998-10-06 2002-02-06 Nippon Mitsubishi Oil Corp Gasoline additive for direct-injection gasoline engine
FR2786490A1 (en) * 1998-11-30 2000-06-02 Atochem Elf Sa POLYBUTYL- OR POLYISOBUTYLAMINES, -HYDRAZINES OR -AZIDES, PROCESS FOR PREPARING THEM AND USES THEREOF AS DETERGENTS IN FUELS
GB2353803A (en) * 1999-09-01 2001-03-07 Ass Octel Gasoline compositions
BR0107777A (en) 2000-01-25 2002-11-12 Akzo Nobel Nv Process for the production of amino polyolefins, and, use of low molecular weight amino polyolefins
BR0110033A (en) 2000-04-14 2003-05-27 Oryxe energy int inc Organic Cetane Perfector
US20060201056A1 (en) * 2000-04-14 2006-09-14 Oryxe Energy International, Inc. Biodiesel fuel additive
US7029506B2 (en) * 2000-04-14 2006-04-18 Jordan Frederick L Organic cetane improver
US7144433B2 (en) * 2001-03-22 2006-12-05 Oryxe Energy International, Inc. Method and composition for using organic, plant-derived, oil-extracted materials in fossil fuels for reduced emissions
US6776897B2 (en) 2001-10-19 2004-08-17 Chevron U.S.A. Thermally stable blends of highly paraffinic distillate fuel component and conventional distillate fuel component
US6846402B2 (en) 2001-10-19 2005-01-25 Chevron U.S.A. Inc. Thermally stable jet prepared from highly paraffinic distillate fuel component and conventional distillate fuel component
US7884058B2 (en) * 2003-09-30 2011-02-08 Chevron Oronite Company Llc Stable colloidal suspensions and lubricating oil compositions containing same
US20050268531A1 (en) * 2004-06-02 2005-12-08 Polar Molecular Corporation Motor fuel additive composition
US20050268532A1 (en) * 2004-06-02 2005-12-08 Polar Molecular Corporation Motor fuel additive composition
US20090158642A1 (en) * 2004-06-02 2009-06-25 Polar Molecular Corporation Motor fuel additive composition
US20050268534A1 (en) * 2004-06-02 2005-12-08 Polar Molecular Corporation Motor fuel additive composition
US20090158643A1 (en) * 2004-06-02 2009-06-25 Polar Molecular Corporation Motor fuel additive composition
US20050268533A1 (en) * 2004-06-02 2005-12-08 Polar Molecular Corporation Motor fuel additive composition
US20050268537A1 (en) * 2004-06-02 2005-12-08 Polar Molecular Corporation Motor fuel additive composition
EP1757673B1 (en) 2005-08-23 2020-04-15 Chevron Oronite Company LLC Lubricating oil composition for internal combustion engines
WO2007037642A1 (en) * 2005-09-29 2007-04-05 Hae Dong Chemical Co., Ltd. Process for the modified polymers by the modification of chlorine containing polymers
US7981846B2 (en) * 2005-11-30 2011-07-19 Chevron Oronite Company Llc Lubricating oil composition with improved emission compatibility
ES2526711T3 (en) 2006-04-26 2015-01-14 Vanderbilt Chemicals, Llc Synergistic antioxidant agent for lubricating compositions
WO2007131104A1 (en) 2006-05-05 2007-11-15 R. T. Vanderbilt Company, Inc. Antioxidant additive for lubricant compositions, comprising organotungstate, diarylamine and organomolybdenum compounds
US20080289249A1 (en) * 2007-05-22 2008-11-27 Peter Wangqi Hou Fuel additive to control deposit formation
US7683017B2 (en) 2007-06-20 2010-03-23 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
WO2009074606A1 (en) * 2007-12-11 2009-06-18 Basf Se Hydrocarbylphenols as intake valve clean-up boosters
US20090163392A1 (en) 2007-12-20 2009-06-25 Boffa Alexander B Lubricating oil compositions comprising a molybdenum compound and a zinc dialkyldithiophosphate
EP2077315B1 (en) 2007-12-20 2012-10-31 Chevron Oronite Company LLC Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant and a diarylamine antioxidant
AP2011005777A0 (en) 2008-12-23 2011-08-31 Ls9 Inc Methods and compositions related to thioesterase enzymes.
FR2947829B1 (en) * 2009-07-10 2012-02-24 Michelin Soc Tech COMPOSITION BASED ON NATURAL RUBBER AND A POLYAMINO COMPOUND
CN105969710A (en) 2009-09-25 2016-09-28 Reg生命科学有限责任公司 Production of fatty acid derivatives
US8933001B2 (en) 2010-03-31 2015-01-13 Chevron Oronite Company Llc Method for improving fluorocarbon elastomer seal compatibility
US8901050B2 (en) 2010-03-31 2014-12-02 Chevron Oronite Company Llc Method for improving copper corrosion performance
US8993496B2 (en) 2010-03-31 2015-03-31 Chevron Oronite Company Llc Method for improving fluorocarbon elastomer seal compatibility
US9150811B2 (en) 2010-03-31 2015-10-06 Cherron Oronite Company LLC Method for improving copper corrosion performance
CN103509614A (en) * 2012-06-21 2014-01-15 中国石油天然气股份有限公司 Preparation and application of macromolecular amine compound for improving fuel detergency
US10017708B2 (en) 2012-09-21 2018-07-10 Exxonmobil Chemical Patents Inc. Lubricant and fuel dispersants and methods of preparation thereof
US9315761B2 (en) 2012-09-21 2016-04-19 Exxonmobil Chemical Patents Inc. Lubricant and fuel dispersants and methods of preparation thereof
CN104479771B (en) * 2014-12-28 2016-05-04 山西华顿实业有限公司 Suppress the composition that boiler alcohol-group fuel nitrogen oxide generates
US10081776B2 (en) 2015-05-11 2018-09-25 Northwestern University Cyclen friction modifiers for boundary lubrication
US20180148663A1 (en) 2016-11-30 2018-05-31 Chevron Japan Ltd. Lubricating oil compositions for motorcycles
US11912877B2 (en) 2022-01-18 2024-02-27 Patrick Brant Aluminum-based coupling agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050043A (en) * 1960-04-01 1962-08-21 California Research Corp Operation of spark-ignition engines
US3231348A (en) * 1961-12-07 1966-01-25 Chevron Res Gasoline fuel containing substituted diethylenetriamines
NL137371C (en) * 1963-08-02

Cited By (671)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844958A (en) * 1965-08-23 1974-10-29 Chevron Res Hydrocarbyl amines for lubricating oil detergents
US3671511A (en) * 1970-04-23 1972-06-20 Lewis R Honnen Process for preparing polyolefin-substituted amines
US3996024A (en) * 1973-06-22 1976-12-07 Chevron Research Company Fuel composition
US4022589A (en) * 1974-10-17 1977-05-10 Phillips Petroleum Company Fuel additive package containing polybutene amine and lubricating oil
US4100086A (en) * 1976-10-26 1978-07-11 Texaco Inc. Dispersant and lube oils containing same
DE2937677A1 (en) * 1978-09-18 1980-04-03 Exxon Research Engineering Co LUBRICANT PREPARATION
US4200518A (en) * 1979-03-22 1980-04-29 Chevron Research Company Heat exchanger anti-foulant
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
US6299655B1 (en) * 1985-03-14 2001-10-09 The Lubrizol Corporation Diesel fuel compositions
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US4746447A (en) * 1986-01-10 1988-05-24 Chevron Research Company Carbonate treated hydrocarbyl-substituted polyamines
US4877416A (en) * 1987-11-18 1989-10-31 Chevron Research Company Synergistic fuel compositions
WO1991003529A1 (en) * 1987-11-18 1991-03-21 Chevron Research Company Synergistic fuel compositions
US4973336A (en) * 1988-06-10 1990-11-27 Gheysens Jean Louis G Fuel additives
EP0351964A1 (en) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
EP0611818A1 (en) 1990-07-31 1994-08-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same
US6346129B1 (en) 1990-12-27 2002-02-12 Chevron Oronite Company Llc Fuel compositions containing hydroxyalkyl-substituted polyamines
US6368370B1 (en) 1990-12-27 2002-04-09 Chevron Oronite Company Llc Fuel compositions containing hydroxyalkyl-substituted amines
WO1992021736A1 (en) 1991-05-30 1992-12-10 The Lubrizol Corporation Two-cycle lubricant and method of using same
US5478367A (en) * 1991-10-11 1995-12-26 Exxon Chemical Patents Inc. Fuel oil compositions
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5455358A (en) * 1992-02-10 1995-10-03 Chevron U.S.A. Inc. Fuel compositions containing alkyl-substituted cyclic urea-substituted amines
US5457211A (en) * 1992-02-10 1995-10-10 Chevron U.S.A. Inc. Hydroxyalkyl-substituted cyclic urea-substituted amines
EP0568873A2 (en) * 1992-05-04 1993-11-10 BASF Aktiengesellschaft Beta-aminonitriles and N-alkyl-1,3-propylenediamines as well as their use as fuel and lubricant additives
US5492641A (en) * 1992-05-04 1996-02-20 Basf Aktiengesellschaft β-aminonitriles and N-alkyl-1,3-propylenediamines and their use as fuel additives and lubricant additives
EP0568873A3 (en) * 1992-05-04 1993-12-29 Basf Ag Beta-aminonitriles and n-alkyl-1,3-propylenediamines as well as their use as fuel and lubricant additives
US5292813A (en) * 1992-10-02 1994-03-08 Exxon Research & Engineering Co. Fullerene-grafted polymers and processes of making
US5292444A (en) * 1992-10-02 1994-03-08 Exxon Research And Engineering Company Lube oil compositions containing fullerene-grafted polymers
US5430105A (en) * 1992-12-17 1995-07-04 Exxon Chemical Patents Inc. Low sediment process for forming borated dispersant
US5663130A (en) * 1992-12-17 1997-09-02 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5498809A (en) * 1992-12-17 1996-03-12 Exxon Chemical Patents Inc. Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US6030930A (en) * 1992-12-17 2000-02-29 Exxon Chemical Patents Inc Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives
WO1994024231A1 (en) * 1993-04-22 1994-10-27 Basf Aktiengesellschaft Poly-1-n-alkene amines and motor fuel and lubricant compositions containing them
AU676310B2 (en) * 1993-04-22 1997-03-06 Basf Aktiengesellschaft Poly-1-N-alkene amines and motor fuel and lubricant compositions containing them
EP0639589A1 (en) * 1993-08-19 1995-02-22 Ferro Corporation Process for the production of fuel additives from chlorinated polybutenes
US5945388A (en) * 1993-09-23 1999-08-31 Lubrizol Adibis Holdings (Uk) Ltd. Lubricating oil compositions
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
EP0695798A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
EP0695799A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Combination of a sulfer compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US6136051A (en) * 1995-07-06 2000-10-24 Chevron Chemical Company Method and composition for reduction of combustion chamber deposits
US5652202A (en) * 1995-08-15 1997-07-29 Exxon Chemical Patents Inc. Lubricating oil compositions
US5558802A (en) * 1995-09-14 1996-09-24 Exxon Chemical Patents Inc Multigrade crankcase lubricants with low temperature pumpability and low volatility
EP0769546A2 (en) 1995-10-18 1997-04-23 The Lubrizol Corporation Antiwear enhancing composition for lubricants and functional fluids
US6468948B1 (en) 1996-06-17 2002-10-22 Infineum Usa L.P. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US6066603A (en) * 1996-06-17 2000-05-23 Exxon Chemical Patents Inc. Polar monomer containing copolymers derived from olefins useful as lubricant and useful as lubricant and fuel oil additivies process for preparation of such copolymers and additives and use thereof
US5811379A (en) * 1996-06-17 1998-09-22 Exxon Chemical Patents Inc. Polymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such polymers and additives and use thereof (PT-1267)
US5810894A (en) * 1996-12-20 1998-09-22 Ferro Corporation Monoamines and a method of making the same
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
US6172015B1 (en) 1997-07-21 2001-01-09 Exxon Chemical Patents, Inc Polar monomer containing copolymers derived from olefins useful as lubricant and fuel oil additives, processes for preparation of such copolymers and additives and use thereof
WO2000009634A1 (en) * 1998-08-10 2000-02-24 The Associated Octel Company Limited Diesel fuel compositions
US6071319A (en) * 1998-12-22 2000-06-06 Chevron Chemical Company Llc Fuel additive compositions containing aromatic esters of polyalkylphenoxyalkanols and aliphatic amines
EP1057811A1 (en) * 1999-06-02 2000-12-06 Chevron Chemical Company LLC Polyalkylpyrrolidines and fuel compositions containing the same
US6860241B2 (en) 1999-06-16 2005-03-01 Dober Chemical Corp. Fuel filter including slow release additive
US6423670B2 (en) 2000-03-20 2002-07-23 Infineum International Ltd. Lubricating oil compositions
WO2002010276A2 (en) 2000-07-31 2002-02-07 The Lubrizol Corporation Polymeric mixture useful as viscosity improver for lubricating oils
US6855674B2 (en) 2000-12-22 2005-02-15 Infineum International Ltd. Hydroxy aromatic Mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US20030173251A1 (en) * 2000-12-22 2003-09-18 Antonio Gutierrez Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US20030122104A1 (en) * 2001-02-12 2003-07-03 Dober Chemical Corporation Liquid replacement systems
US6525004B1 (en) 2001-05-01 2003-02-25 Infineum International Inc. Combustion improving additive for small engine lubricating oils
US6878676B1 (en) 2001-05-08 2005-04-12 Crompton Corporation Nanosized particles of molybdenum sulfide and derivatives, method for its preparation and uses thereof as lubricant additive
US20050065044A1 (en) * 2001-05-08 2005-03-24 Migdal Cyril A Nanosized particles of molybdenum sulfide and derivatives,method for its preparation and uses thereof as lubricant additive
US6824671B2 (en) 2001-05-17 2004-11-30 Exxonmobil Chemical Patents Inc. Low noack volatility poly α-olefins
US6949688B2 (en) 2001-05-17 2005-09-27 Exxonmobil Chemical Patents Inc. Low Noack volatility poly α-olefins
US20020193650A1 (en) * 2001-05-17 2002-12-19 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US20050045527A1 (en) * 2001-05-17 2005-03-03 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US7581558B2 (en) 2001-08-24 2009-09-01 Cummins Filtration Ip Inc. Controlled release of additives in fluid systems
US7938277B2 (en) 2001-08-24 2011-05-10 Dober Chemical Corporation Controlled release of microbiocides
US6827750B2 (en) 2001-08-24 2004-12-07 Dober Chemical Corp Controlled release additives in fuel systems
US6835218B1 (en) 2001-08-24 2004-12-28 Dober Chemical Corp. Fuel additive compositions
US20050019236A1 (en) * 2001-08-24 2005-01-27 Harold Martin Controlled release of additives in fluid systems
US8109287B2 (en) 2001-08-24 2012-02-07 Cummins Filtration Ip, Inc. Controlled release of additives in fluid systems
US20080296234A1 (en) * 2001-08-24 2008-12-04 Dober Chemical Corporation Controlled release of microbiocides
US20040091654A1 (en) * 2001-08-24 2004-05-13 Fleetguard, Inc. Controlled release of additives in cooling systems
US7001531B2 (en) 2001-08-24 2006-02-21 Dober Chemical Corp. Sustained release coolant additive composition
US20070000831A1 (en) * 2001-08-24 2007-01-04 Fleetguard, Inc. Controlled release of additives in cooling systems
US7591279B2 (en) 2001-08-24 2009-09-22 Cummins Filtration Ip Inc. Controlled release of additives in fluid systems
US20070241042A1 (en) * 2001-08-24 2007-10-18 Dober Chemical Corporation Controlled release of additives in fluid systems
EP2272940A1 (en) 2001-09-14 2011-01-12 Afton Chemical Intangibles LLC Fuels compositions for direct injection gasoline engines
US20030079399A1 (en) * 2001-09-14 2003-05-01 Malfer Dennis J. Fuels compositions for direct injection gasoline engines
EP1331376A2 (en) 2002-01-23 2003-07-30 Chevron Oronite Company LLC Method for removing engine deposits in a reciprocating internal combustion engine
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US6573223B1 (en) 2002-03-04 2003-06-03 The Lubrizol Corporation Lubricating compositions with good thermal stability and demulsibility properties
US6689723B2 (en) 2002-03-05 2004-02-10 Exxonmobil Chemical Patents Inc. Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same
US6660050B1 (en) 2002-05-23 2003-12-09 Chevron U.S.A. Inc. Method for controlling deposits in the fuel reformer of a fuel cell system
EP2284248A2 (en) 2002-07-16 2011-02-16 The Lubrizol Corporation Slow release lubricant additives gel
US6869917B2 (en) 2002-08-16 2005-03-22 Exxonmobil Chemical Patents Inc. Functional fluid lubricant using low Noack volatility base stock fluids
US20040033908A1 (en) * 2002-08-16 2004-02-19 Deckman Douglas E. Functional fluid lubricant using low Noack volatility base stock fluids
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2436753A1 (en) 2002-10-04 2012-04-04 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2366762A1 (en) 2002-10-04 2011-09-21 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2460870A1 (en) 2002-10-04 2012-06-06 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2243816A1 (en) 2003-06-25 2010-10-27 The Lubrizol Corporation Gel additives for fuel that reduce soot and/or emissions from engines
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20070054813A1 (en) * 2003-09-25 2007-03-08 Chip Hewette Boron free automotive gear oil
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US9267093B2 (en) 2003-11-10 2016-02-23 Afton Chemical Corporation Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
EP2230292A1 (en) 2003-11-10 2010-09-22 Afton Chemical Corporation Methods of lubricating transmissions
US20080009426A1 (en) * 2003-11-10 2008-01-10 Iyer Ramnath N Lubricant Compositions and Methods Comprising Dispersant and Detergent
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
US20100279901A1 (en) * 2003-11-10 2010-11-04 Iyer Ramnath N Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
EP1531175A2 (en) 2003-11-12 2005-05-18 Afton Chemical Corporation Compositions and methods for improved friction durability in power transmission fluids
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
US20080090744A1 (en) * 2003-11-12 2008-04-17 Saathoff Lee D Compositions and Methods for Improved Friction Durability in Power Transmission Fluids
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20070111908A1 (en) * 2004-07-19 2007-05-17 Lam William Y Titanium-containing lubricating oil composition
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7879774B2 (en) 2004-07-19 2011-02-01 Afton Chemical Corporation Titanium-containing lubricating oil composition
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
EP2116590A1 (en) 2005-02-18 2009-11-11 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US20060196111A1 (en) * 2005-03-04 2006-09-07 Colucci William J Fuel additive composition
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US20060205615A1 (en) * 2005-03-14 2006-09-14 Esche Carl K Jr Additives and lubricant formulations for improved antioxidant properties
US8557752B2 (en) 2005-03-23 2013-10-15 Afton Chemical Corporation Lubricating compositions
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
US7618928B2 (en) 2005-08-31 2009-11-17 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
US20070049503A1 (en) * 2005-08-31 2007-03-01 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
US20070111906A1 (en) * 2005-11-12 2007-05-17 Milner Jeffrey L Relatively low viscosity transmission fluids
US7709423B2 (en) 2005-11-16 2010-05-04 Afton Chemical Corporation Additives and lubricant formulations for providing friction modification
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US20070132274A1 (en) * 2005-12-09 2007-06-14 Lam William Y Titanium-containing lubricating oil composition
US7776800B2 (en) 2005-12-09 2010-08-17 Afton Chemical Corporation Titanium-containing lubricating oil composition
US7632788B2 (en) 2005-12-12 2009-12-15 Afton Chemical Corporation Nanosphere additives and lubricant formulations containing the nanosphere additives
US20070135317A1 (en) * 2005-12-12 2007-06-14 Tze-Chi Jao Nanosphere additives and lubricant formulations containing the nanosphere additives
US7767632B2 (en) 2005-12-22 2010-08-03 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
EP2371933A1 (en) 2006-02-06 2011-10-05 The Lubrizol Corporation Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof
US20070259792A1 (en) * 2006-03-22 2007-11-08 Null Volker K Functional fluid compositions
US7867958B2 (en) 2006-04-28 2011-01-11 Afton Chemical Corporation Diblock monopolymers as lubricant additives and lubricant formulations containing same
US20070254820A1 (en) * 2006-04-28 2007-11-01 Tze-Chi Jao Diblock monopolymers as lubricant additives and lubricant formulations containing same
US20080026973A1 (en) * 2006-05-03 2008-01-31 Nelson David C Lubricating oil composition
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US7879775B2 (en) 2006-07-14 2011-02-01 Afton Chemical Corporation Lubricant compositions
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
EP3339404A1 (en) 2006-07-18 2018-06-27 Infineum International Limited Lubricating oil compositions
WO2008013698A1 (en) 2006-07-21 2008-01-31 Exxonmobil Research And Engineering Company Method for lubricating heavy duty geared apparatus
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US7833953B2 (en) 2006-08-28 2010-11-16 Afton Chemical Corporation Lubricant composition
US20080108531A1 (en) * 2006-11-08 2008-05-08 The Lubrizol Corporation Viscosity Modifiers in Controlled Release Lubricant Additive Gels
US7833955B2 (en) 2006-11-08 2010-11-16 The Lubrizol Corporation Viscosity modifiers in controlled release lubricant additive gels
EP2455406A1 (en) 2006-11-09 2012-05-23 The Lubrizol Corporation Quaternary Ammonium Salt of a Polyalkene-Substituted Amine Compound
WO2008060888A2 (en) 2006-11-09 2008-05-22 The Lubrizol Corporation Quaternary ammonium salt of a polyalkene-substituted amine compound
EP1930401A1 (en) 2006-11-21 2008-06-11 Chevron Oronite Company LLC Functional fluids comprising alkyl toluene sulfonates
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
US20080132432A1 (en) * 2006-12-01 2008-06-05 Mathur Naresh C Additives and lubricant formulations for providing friction modification
US7772167B2 (en) 2006-12-06 2010-08-10 Afton Chemical Corporation Titanium-containing lubricating oil composition
US20080139429A1 (en) * 2006-12-06 2008-06-12 Guinther Gregory H Titanium-containing lubricating oil composition
DE102007056248A1 (en) 2006-12-08 2008-07-10 Afton Chemical Corp. Additive and lubricant formulations for improved antiwear properties
US8425772B2 (en) 2006-12-12 2013-04-23 Cummins Filtration Ip, Inc. Filtration device with releasable additive
EP1942177A2 (en) 2006-12-19 2008-07-09 Chevron Oronite Company LLC Lubricating oil providing enhanced piston cleanliness
EP1947164A1 (en) 2006-12-21 2008-07-23 Chevron Oronite Technology B.V. Engine lubricant with enhanced thermal stability
US20080161213A1 (en) * 2007-01-03 2008-07-03 Tze-Chi Jao Nanoparticle additives and lubricant formulations containing the nanoparticle additives
US8741821B2 (en) 2007-01-03 2014-06-03 Afton Chemical Corporation Nanoparticle additives and lubricant formulations containing the nanoparticle additives
DE102007023939A1 (en) 2007-01-03 2008-07-10 Afton Chemical Corp. Nanoparticle additives and lubricant formulations containing the nanoparticle additives
DE102008005330A1 (en) 2007-01-31 2008-08-07 Afton Chemical Corp. Lubricant composition for biodiesel fuel engine uses
US20080182768A1 (en) * 2007-01-31 2008-07-31 Devlin Cathy C Lubricant composition for bio-diesel fuel engine applications
EP1959003A2 (en) 2007-02-08 2008-08-20 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
US7897548B2 (en) 2007-03-15 2011-03-01 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
DE102008005874A1 (en) 2007-03-15 2008-09-18 Afton Chemical Corp. Additive and lubricant formulations for improved antiwear properties
DE102007061422A1 (en) 2007-03-26 2008-10-02 Afton Chemical Corp. Lubricating oil composition for improved oxidation, viscosity increase, oil consumption and piston deposition control
US20080236538A1 (en) * 2007-03-26 2008-10-02 Lam William Y Lubricating oil composition for improved oxidation, viscosity increase, oil consumption, and piston deposit control
US20080280796A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved catalyst performance
DE102008009042A1 (en) 2007-05-08 2008-11-13 Afton Chemical Corp. Additive and lubricant formulations for improved phosphorus retention properties
US20080277203A1 (en) * 2007-05-08 2008-11-13 Guinther Gregory H Additives and lubricant formulations for improved phosphorus retention properties
US8048834B2 (en) 2007-05-08 2011-11-01 Afton Chemical Corporation Additives and lubricant formulations for improved catalyst performance
EP2000523A1 (en) 2007-05-30 2008-12-10 Chevron Oronite S.A. Lubricating oil with enhanced protection against wear and corrosion
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
EP2302020A1 (en) 2007-07-28 2011-03-30 Innospec Limited Use of additives for improving oxidation stability of a fuel oil composition
US20090042752A1 (en) * 2007-08-09 2009-02-12 Malcolm Waddoups Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters
EP2031045A1 (en) 2007-08-09 2009-03-04 Infineum International Limited Lubricant compositions with reduced phosphorous content for engines having catalytic converters
US8278254B2 (en) 2007-09-10 2012-10-02 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties
US20090069205A1 (en) * 2007-09-10 2009-03-12 Devlin Mark T Additives and lubricant formulations having improved antiwear properties
EP2039741A1 (en) 2007-09-17 2009-03-25 Afton Chemical Corporation Additives and lubricant formulations for improved catalyst performance
EP2042582A2 (en) 2007-09-24 2009-04-01 Afton Chemical Corporation Surface passivation and to methods for the reduction of fuel thermal degradation deposits
US7737094B2 (en) 2007-10-25 2010-06-15 Afton Chemical Corporation Engine wear protection in engines operated using ethanol-based fuel
US20090111722A1 (en) * 2007-10-25 2009-04-30 Guinther Gregory H Engine wear protection in engines operated using ethanol-based fuel
US7897552B2 (en) 2007-11-30 2011-03-01 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
EP2067843A1 (en) 2007-11-30 2009-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US20090143265A1 (en) * 2007-11-30 2009-06-04 Ellington Joruetta R Additives and lubricant formulations for improved antioxidant properties
US20090156445A1 (en) * 2007-12-13 2009-06-18 Lam William Y Lubricant composition suitable for engines fueled by alternate fuels
EP2072611A1 (en) 2007-12-13 2009-06-24 Afton Chemical Corporation Lubricant composition suitable for engines fueled by alternate fuels
EP2077316A2 (en) 2007-12-17 2009-07-08 Infineum International Limited Lubricant compositions with low HTHS for a given SAE viscosity grade
EP2075264A1 (en) 2007-12-26 2009-07-01 Infineum International Limited Method of forming polyalkene substituted carboxylic acid compositions
EP2083063A1 (en) 2008-01-22 2009-07-29 Infineum International Limited Lubricating oil composition
US20090192061A1 (en) * 2008-01-24 2009-07-30 Boegner Philip J Olefin copolymer dispersant vi improver and lubricant compositions and uses thereof
US8420583B2 (en) 2008-01-24 2013-04-16 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2083024A1 (en) 2008-01-24 2009-07-29 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2090642A1 (en) 2008-02-08 2009-08-19 Infineum International Limited Engine lubrication
US8703669B2 (en) 2008-03-11 2014-04-22 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
US20090233822A1 (en) * 2008-03-11 2009-09-17 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
DE102009001301A1 (en) 2008-03-11 2009-09-24 Volkswagen Ag Method for lubricating a component only for the clutch of an automatic transmission, which requires lubrication
US8546311B2 (en) 2008-03-11 2013-10-01 Volkswagen Aktiengesellsschaft Method for lubricating a clutch-only automatic transmission component requiring lubrication
DE102009012567A1 (en) 2008-03-11 2009-10-01 Afton Chemical Corp. Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent
WO2009119831A1 (en) 2008-03-28 2009-10-01 富士フイルム株式会社 Composition and method for forming coating film
DE102009019952A1 (en) 2008-05-23 2009-12-10 Afton Chemical Corp. Controlled release of additives in lubricant compositions for gas turbines
US8591747B2 (en) 2008-05-27 2013-11-26 Dober Chemical Corp. Devices and methods for controlled release of additive compositions
US20090301968A1 (en) * 2008-05-27 2009-12-10 Dober Chemical Corporation Devices and methods for controlled release of additive compositions
US8702995B2 (en) 2008-05-27 2014-04-22 Dober Chemical Corp. Controlled release of microbiocides
US7883638B2 (en) 2008-05-27 2011-02-08 Dober Chemical Corporation Controlled release cooling additive compositions
US20090304868A1 (en) * 2008-05-27 2009-12-10 Dober Chemical Corporation Controlled release cooling additive composition
US20090294345A1 (en) * 2008-05-27 2009-12-03 Dober Chemical Corporation Controlled release of microbiocides
US8008237B2 (en) 2008-06-18 2011-08-30 Afton Chemical Corporation Method for making a titanium-containing lubricant additive
US20090318318A1 (en) * 2008-06-18 2009-12-24 Afton Chemical Corporation Method for making a titanium-containing lubricant additive
EP2135925A1 (en) 2008-06-18 2009-12-23 Afton Chemical Corporation Method for making a titanium-containing lubricant additive
EP2143781A1 (en) 2008-06-23 2010-01-13 Afton Chemical Corporation Friction modifiers for slideway applications
US20090318319A1 (en) * 2008-06-23 2009-12-24 Afton Chemical Corporation Friction modifiers for slideway applications
US20100004382A1 (en) * 2008-07-01 2010-01-07 Exxonmobil Research And Engineering Company Emulsion compositions with a polymeric emulsifier
US8183314B2 (en) 2008-07-01 2012-05-22 Exxonmobil Research And Engineering Company Emulsion compositions with a polymeric emulsifier
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
US8633142B2 (en) 2008-07-31 2014-01-21 Shell Oil Company Poly (hydroxycarboxylic acid) amide salt derivative and lubricating composition containing it
US20110207640A1 (en) * 2008-07-31 2011-08-25 Jan Elsa Eugenia Carty Poly (hydroxycarboxylic acid) amide salt derivative and lubricating composition containing it
US20100024286A1 (en) * 2008-07-31 2010-02-04 Smith Susan Jane Liquid fuel compositions
US20100024287A1 (en) * 2008-07-31 2010-02-04 Smith Susan Jane Liquid fuel compositions
EP2154230A1 (en) 2008-08-08 2010-02-17 Afton Chemical Corporation Lubricant additive compositions having improved viscosity index increasing properties
US20100035774A1 (en) * 2008-08-08 2010-02-11 Afton Chemical Corporation Lubricant additive compositions having improved viscosity index increase properties
US8778857B2 (en) 2008-08-08 2014-07-15 Afton Chemical Corporation Lubricant additive compositions having improved viscosity index increase properties
EP2196522A1 (en) 2008-12-09 2010-06-16 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties
US8211840B2 (en) 2008-12-09 2012-07-03 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US20100144563A1 (en) * 2008-12-09 2010-06-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US8465560B1 (en) 2009-02-05 2013-06-18 Butamax Advanced Biofuels Llc Gasoline deposit control additive composition
WO2010091069A1 (en) 2009-02-05 2010-08-12 Butamax™ Advanced Biofuels LLC Gasoline deposit control additive compositions
WO2010093519A1 (en) 2009-02-16 2010-08-19 Chemtura Corporation Fatty sorbitan ester based friction modifiers
US20100206260A1 (en) * 2009-02-18 2010-08-19 Chevron Oronite Company Llc Method for preventing exhaust valve seat recession
WO2010096472A2 (en) 2009-02-18 2010-08-26 Chevron Oronite Company Llc Method for preventing exhaust valve seat recession
WO2010096325A1 (en) 2009-02-18 2010-08-26 The Lubrizol Corporation Amine derivatives as friction modifiers in lubricants
US8969273B2 (en) 2009-02-18 2015-03-03 Chevron Oronite Company Llc Lubricating oil compositions
EP2236590A1 (en) 2009-04-01 2010-10-06 Infineum International Limited Lubricating oil composition
WO2010115594A1 (en) 2009-04-07 2010-10-14 Infineum International Limited Marine engine lubrication
US8377856B2 (en) 2009-05-14 2013-02-19 Afton Chemical Corporation Extended drain diesel lubricant formulations
US20100292112A1 (en) * 2009-05-14 2010-11-18 Afton Chemical Corporation Extended drain diesel lubricant formulations
US20100292113A1 (en) * 2009-05-15 2010-11-18 Afton Chemical Corporation Lubricant formulations and methods
EP2251401A2 (en) 2009-05-15 2010-11-17 Afton Chemical Corporation Lubricant formulations and methods
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
US9663743B2 (en) 2009-06-10 2017-05-30 Afton Chemical Corporation Lubricating method and composition for reducing engine deposits
EP2261311A1 (en) 2009-06-10 2010-12-15 Afton Chemical Corporation Lubricating method and composition for reducing engine deposits
US20100317552A1 (en) * 2009-06-10 2010-12-16 Afton Chemical Corporation Lubricating method and composition for reducing engine deposits
WO2010147993A1 (en) 2009-06-16 2010-12-23 Chevron Phillips Chemical Company Lp Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends
EP3587458A1 (en) 2009-06-16 2020-01-01 Chevron Phillips Chemical Company LP Compositions comprising polyalphaolefins
WO2010149712A1 (en) 2009-06-25 2010-12-29 Shell Internationale Research Maatschappij B.V. Lubricating composition
US8549897B2 (en) 2009-07-24 2013-10-08 Chevron Oronite S.A. System and method for screening liquid compositions
EP2278327A1 (en) 2009-07-24 2011-01-26 Chevron Oronite S.A. System and Method for Screening Liquid Compositions
US20110016954A1 (en) * 2009-07-24 2011-01-27 Chevron Oronite S.A. System and method for screening liquid compositions
WO2011017186A1 (en) 2009-08-04 2011-02-10 The Lubrizol Corporation Compositions with fast and slow release components
EP2290041A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
US8288326B2 (en) 2009-09-02 2012-10-16 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
US20110053814A1 (en) * 2009-09-02 2011-03-03 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
EP2913387A1 (en) 2009-09-02 2015-09-02 Chevron Oronite Company LLC Natural gas engine lubricating oil compositions
WO2011026990A1 (en) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Lubricating compositions
US8207099B2 (en) 2009-09-22 2012-06-26 Afton Chemical Corporation Lubricating oil composition for crankcase applications
US20110067662A1 (en) * 2009-09-22 2011-03-24 Afton Chemical Corporation Lubricating oil composition for crankcase applications
US8415284B2 (en) 2009-11-05 2013-04-09 Afton Chemical Corporation Olefin copolymer VI improvers and lubricant compositions and uses thereof
US20110105371A1 (en) * 2009-11-05 2011-05-05 Afton Chemical Corporation Olefin copolymer vi improvers and lubricant compositions and uses thereof
EP2325291A1 (en) 2009-11-05 2011-05-25 Afton Chemical Corporation Olefin Copolymer VI improvers and lubricant compositions and uses thereof
US8486877B2 (en) 2009-11-18 2013-07-16 Chevron Oronite Company Llc Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals
US20110118160A1 (en) * 2009-11-18 2011-05-19 Chevron Oronite Company Llc Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals
US9062273B2 (en) 2009-12-15 2015-06-23 Chevron Oronite Company Llc Lubricating oil compositions containing titanium complexes
US8969265B2 (en) 2009-12-15 2015-03-03 Chevron Oronite Company Llc Lubricating oil compositions
US20110143979A1 (en) * 2009-12-15 2011-06-16 Chevron Oronite Company Llc Lubricating oil compositions
US8709984B2 (en) 2009-12-15 2014-04-29 Chevron Oronite Company Llc Lubricating oil compositions
US9365794B2 (en) 2010-02-19 2016-06-14 Infineum International Limited Wet friction clutch—lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
US9725673B2 (en) 2010-03-25 2017-08-08 Afton Chemical Corporation Lubricant compositions for improved engine performance
EP2371935A1 (en) 2010-03-25 2011-10-05 Afton Chemical Corporation Lubricant compositions for improved engine performance
US20110237476A1 (en) * 2010-03-25 2011-09-29 Afton Chemical Corporation Lubricant compositions for improved engine performance
US8841243B2 (en) 2010-03-31 2014-09-23 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
US9932536B2 (en) 2010-05-10 2018-04-03 Innospec Limited Gasoline composition, method and use
US9493720B2 (en) 2010-05-10 2016-11-15 Innospec Limited Gasoline composition, method and use
WO2011143051A1 (en) 2010-05-12 2011-11-17 The Lubrizol Corporation Tartaric acid derivatives in hths fluids
WO2011143418A1 (en) 2010-05-12 2011-11-17 Exxonmobil Research And Engineering Company Method for reducing one or more of deposits and friction of a lubricating oil
EP2402421A2 (en) 2010-06-29 2012-01-04 Chevron Oronite Technology B.V. Trunk Piston Engine Lubricating Oil Compositions
US8318643B2 (en) 2010-06-29 2012-11-27 Cherron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
EP3070153A1 (en) 2010-09-07 2016-09-21 The Lubrizol Corporation Hydroxychroman derivatives as antioxidants
WO2012033668A1 (en) 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
WO2012051075A2 (en) 2010-10-12 2012-04-19 Chevron Oronite Company Llc Lubricating composition containing multifunctional borated hydroxylated amine salt of a hindered phenolic acid
US8796192B2 (en) 2010-10-29 2014-08-05 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions
US8632638B2 (en) 2010-11-19 2014-01-21 Chevron Oronite Company Llc Method for cleaning deposits from an engine fuel delivery system
US8703680B2 (en) 2010-11-24 2014-04-22 Chevron Oronite Company Llc Lubricating composition containing friction modifier blend
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
US8716202B2 (en) 2010-12-14 2014-05-06 Chevron Oronite Company Llc Method for improving fluorocarbon elastomer seal compatibility
EP3348626A1 (en) 2010-12-22 2018-07-18 Rhodia Operations Use of a fuel additive composition based on a dispersion of particles of iron and a detergent
WO2012084906A1 (en) 2010-12-22 2012-06-28 Rhodia Operations Fuel additive composition containing a dispersion of iron particles and a detergent
US8426608B2 (en) 2011-01-21 2013-04-23 Chevron Oronite Company Llc Process for preparation of high molecular weight molybdenum succinimide complexes
WO2012099736A2 (en) 2011-01-21 2012-07-26 Chevron Oronite Company Llc Improved process for preparation of high molecular weight molybdenum succinimide complexes
US8476460B2 (en) 2011-01-21 2013-07-02 Chevron Oronite Company Llc Process for preparation of low molecular weight molybdenum succinimide complexes
WO2012099734A2 (en) 2011-01-21 2012-07-26 Chevron Oronite Company Llc Improved process for preparation of low molecular weight molybdenum succinimide complexes
US8333945B2 (en) 2011-02-17 2012-12-18 Afton Chemical Corporation Nanoparticle additives and lubricant formulations containing the nanoparticle additives
EP2489637A1 (en) 2011-02-17 2012-08-22 Afton Chemical Corporation Cerium oxide nanoparticle additives and lubricant formulations containing the nanoparticle additives
US8702968B2 (en) 2011-04-05 2014-04-22 Chevron Oronite Technology B.V. Low viscosity marine cylinder lubricating oil compositions
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
EP2524958A1 (en) 2011-05-20 2012-11-21 Afton Chemical Corporation Lubricant compositions containing a heteroaromatic compound
US9090847B2 (en) 2011-05-20 2015-07-28 Afton Chemical Corporation Lubricant compositions containing a heteroaromatic compound
WO2012163935A2 (en) 2011-05-30 2012-12-06 Shell Internationale Research Maatschappij B.V. Liquid fuel compositions
WO2013003406A1 (en) 2011-06-29 2013-01-03 Exxonmobil Research And Engineering Company Low viscosity engine oil with superior engine wear protection
US8586520B2 (en) 2011-06-30 2013-11-19 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013003405A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyalkylene glycol mono ethers
WO2013003394A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyetheramines
WO2013003392A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
US10538714B2 (en) 2011-07-12 2020-01-21 Total Marketing Services Additive compositions that improve the stability and the engine performances of diesel fuels
US10081773B2 (en) 2011-07-12 2018-09-25 Total Marketing Services Additive compositions that improve the stability and the engine performances of diesel fuels
WO2013007738A1 (en) 2011-07-12 2013-01-17 Total Raffinage Marketing Additive compositions that improve the stability and the engine performances of diesel fuels
EP2732012B1 (en) 2011-07-12 2015-12-09 Total Marketing Services Compositions of additives improving stability and engine performance of diesel fuels.
WO2013013026A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Carboxylic pyrrolidinones and methods of use thereof
WO2013012987A1 (en) 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof
US8927469B2 (en) 2011-08-11 2015-01-06 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
EP2557144A1 (en) 2011-08-11 2013-02-13 Afton Chemical Corporation Lubricant compositions containing a functionalized dispersant
WO2013043332A1 (en) 2011-09-23 2013-03-28 The Lubrizol Corporation Quaternary ammonium salts in heating oils
WO2013055480A1 (en) 2011-10-10 2013-04-18 Exxonmobil Research And Engineering Company Low viscosity engine oil compositions
WO2013055481A1 (en) 2011-10-10 2013-04-18 Exxonmobil Research And Engineering Company High efficiency engine oil compositions
WO2013055482A1 (en) 2011-10-10 2013-04-18 Exxonmobil Research And Engineering Company Lubricating compositions
WO2013066915A1 (en) 2011-11-01 2013-05-10 Exxonmobil Research And Engineering Company Lubricants with improved low-temperature fuel economy
US8933002B2 (en) 2011-11-10 2015-01-13 Chevron Oronite Company Llc Lubricating oil compositions
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
WO2013074498A1 (en) 2011-11-14 2013-05-23 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013082206A1 (en) 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
US9068134B2 (en) 2011-12-02 2015-06-30 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
EP2604676A1 (en) 2011-12-16 2013-06-19 Chevron Oronite Technology B.V. Trunk piston engine lubricating oil compositions
US9206374B2 (en) 2011-12-16 2015-12-08 Chevron Oronite Sas Trunk piston engine lubricating oil compositions
US9453173B2 (en) 2011-12-21 2016-09-27 Shell Oil Company Method and composition for inhibiting foam in a hydrocarbon mixture
US9150472B2 (en) 2011-12-21 2015-10-06 Shell Oil Company Method and composition for inhibiting asphaltene deposition in a hydrocarbon mixture
US9416307B2 (en) 2011-12-21 2016-08-16 Shell Oil Company Method and composition for inhibiting wax in a hydrocarbon mixture
WO2013092533A1 (en) 2011-12-21 2013-06-27 Total Raffinage Marketing Additive compositions that improve the lacquering resistance of superior quality diesel or biodiesel fuels
WO2013096532A1 (en) 2011-12-22 2013-06-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9249091B2 (en) 2011-12-27 2016-02-02 Chevron Oronite Company Llc Post-treated sulfurized salt of an alkyl-substituted hydroxyaromatic composition
WO2013101256A2 (en) 2011-12-30 2013-07-04 Butamax (Tm) Advanced Biofuels Llc Corrosion inhibitor compositions for oxygenated gasolines
US9587193B2 (en) 2012-02-17 2017-03-07 Total Marketing Services Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
WO2013120985A1 (en) 2012-02-17 2013-08-22 Total Raffinage Marketing Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
WO2013142110A1 (en) 2012-03-22 2013-09-26 Exxonmobil Research And Engineering Company Novel antioxidant combination and synthetic base oils containing the same
US9150812B2 (en) 2012-03-22 2015-10-06 Exxonmobil Research And Engineering Company Antioxidant combination and synthetic base oils containing the same
WO2013151911A1 (en) 2012-04-04 2013-10-10 The Lubrizol Corporation Bearing lubricants for pulverizing equipment
US9315756B2 (en) 2012-04-06 2016-04-19 Exxonmobil Research And Engineering Company Bio-feeds based hybrid group V base stocks and method of production thereof
WO2013165792A1 (en) 2012-05-02 2013-11-07 Lubrizol Advanced Materials, Inc. Aromatic dispersant composition
US8703666B2 (en) 2012-06-01 2014-04-22 Exxonmobil Research And Engineering Company Lubricant compositions and processes for preparing same
WO2013181318A1 (en) 2012-06-01 2013-12-05 Exxonmobil Research And Engineering Company Lubricant compostions and processes for preparing same
WO2013182581A1 (en) 2012-06-06 2013-12-12 Evonik Oil Additives Gmbh Fuel efficient lubricating oils
WO2014008121A1 (en) 2012-07-02 2014-01-09 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
US9228149B2 (en) 2012-07-02 2016-01-05 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
EP2687582A1 (en) 2012-07-18 2014-01-22 Afton Chemical Corporation Lubricant compositions for direct injection engines
US9422497B2 (en) 2012-09-21 2016-08-23 Exxonmobil Research And Engineering Company Synthetic lubricant basestocks and methods of preparation thereof
EP3489332A1 (en) 2012-10-23 2019-05-29 The Lubrizol Corporation Diesel detergent without a low molecular weight penalty
WO2014066344A1 (en) 2012-10-23 2014-05-01 The Lubrizol Corporation Diesel detergent without a low molecular weight penalty
US9487729B2 (en) 2012-10-24 2016-11-08 Exxonmobil Chemical Patents Inc. Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
WO2014066444A1 (en) 2012-10-24 2014-05-01 Exxonmobil Research And Engineering Comapny Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
WO2014065984A1 (en) 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
EP2727984A1 (en) 2012-11-02 2014-05-07 Infineum International Limited Marine engine lubrication
EP2735603A1 (en) 2012-11-21 2014-05-28 Infineum International Limited Marine engine lubrication
WO2014088814A1 (en) 2012-12-07 2014-06-12 The Lubrizol Corporation Pyran dispersants
WO2014107314A1 (en) 2013-01-03 2014-07-10 Exxonmobil Research And Engineering Company Lubricating compositions having improved shear stability
WO2014107315A1 (en) 2013-01-04 2014-07-10 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
EP2765179A1 (en) 2013-02-07 2014-08-13 Infineum International Limited Marine engine lubrication
WO2014158533A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Lubricating composition providing high wear resistance
US9663727B2 (en) 2013-03-14 2017-05-30 Exxonmobil Research And Engineering Company Functionalized polymers containing polyamine succinimide for antifouling in hydrocarbon refining processes
US20140262950A1 (en) * 2013-03-14 2014-09-18 Exxonmobil Research And Engineering Company Hydrohalogenation of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US9617482B2 (en) 2013-03-14 2017-04-11 Exxonmobil Research And Engineering Company Functionalized polymers containing polyamine succinimide for demulsification in hydrocarbon refining processes
US9334460B2 (en) 2013-03-14 2016-05-10 Exxonmobil Research And Engineering Company Ring opening cross metathesis of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US9212326B2 (en) * 2013-03-14 2015-12-15 Exxonmobil Research And Engineering Company Hydrohalogenation of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
WO2014158602A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Method for improving emulsion characteristics of engine oils
US9777231B2 (en) 2013-03-14 2017-10-03 Exxonmobil Research And Engineering Company Hydrohalogenation of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US9540576B2 (en) 2013-03-14 2017-01-10 Exxonmobil Research And Engineering Company Hydrohalogenation of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US9745528B2 (en) 2013-03-14 2017-08-29 Exxonmobil Research And Engineering Company Ring opening cross metathesis of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
US9714393B2 (en) 2013-03-14 2017-07-25 Exxonmobil Research And Engineering Company Ring opening cross metathesis of vinyl terminated polymers and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes
WO2014149406A1 (en) 2013-03-15 2014-09-25 Exxonmobil Research And Engineering Company Method for improving thermal -oxidative stability and elastomer compatibility
US9062269B2 (en) 2013-03-15 2015-06-23 Exxonmobil Research And Engineering Company Method for improving thermal-oxidative stability and elastomer compatibility
US9434906B2 (en) 2013-03-25 2016-09-06 Chevron Oronite Company, Llc Marine diesel engine lubricating oil compositions
WO2014193692A1 (en) 2013-05-28 2014-12-04 The Lubrizol Corporation Asphaltene inhibition
US11111449B2 (en) 2013-06-07 2021-09-07 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP4442792A2 (en) 2013-06-07 2024-10-09 Basf Se Use with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid of quaternised nitrogen compounds as additives in fuels and lubricants
US10407634B2 (en) 2013-06-07 2019-09-10 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP3205705A1 (en) 2013-06-07 2017-08-16 Basf Se Alkylene oxide and hydrocarbyl-substituted polycarboxylic acid quaternised alkylamine as additives in fuels and lubricants and their use
US11912950B2 (en) 2013-06-07 2024-02-27 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP3653689A1 (en) 2013-06-07 2020-05-20 Basf Se Use with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid of quaternised nitrogen compounds as additives in fuels and lubricants
US10676685B2 (en) 2013-06-07 2020-06-09 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP4190882A1 (en) 2013-06-07 2023-06-07 Basf Se Use with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid of quaternised nitrogen compounds as additives in fuels and lubricants
US10626341B2 (en) 2013-07-26 2020-04-21 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
EP3575386A1 (en) 2013-07-26 2019-12-04 Innospec Limited Fuel compositions comprising a quaternary ammonium compound as an additive
US10351791B2 (en) 2013-07-26 2019-07-16 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
US11066617B2 (en) 2013-07-26 2021-07-20 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
EP3575385A1 (en) 2013-07-26 2019-12-04 Innospec Limited Method for preparing a fuel composition comprising a quaternary ammonium compound
WO2015031043A1 (en) 2013-08-29 2015-03-05 Lubrizol Advanced Materials, Inc. Non-fused aromatic dispersant composition
US10815444B2 (en) 2013-09-20 2020-10-27 Basf Se Use of specific derivatives of quaternized nitrogen compounds as additives in fuels and lubricants
US10370610B2 (en) 2013-09-20 2019-08-06 Basf Se Use of specific derivatives of quaternized nitrogen compounds as additives in fuels and lubricants
EP3483234A1 (en) 2013-09-20 2019-05-15 Basf Se Use of specialised derivatives of quaternised nitrogen compounds as additives in fuels and lubricants
EP2851412A1 (en) 2013-09-24 2015-03-25 Infineum International Limited Marine engine lubrication
WO2015047939A1 (en) 2013-09-25 2015-04-02 3M Innovative Properties Company Composite ceramic abrasive polishing solution
WO2015048011A1 (en) 2013-09-25 2015-04-02 3M Innovative Properties Company Multi-layered polishing pads
US10293458B2 (en) 2013-09-25 2019-05-21 3M Innovative Properties Company Composite ceramic abrasive polishing solution
US10071459B2 (en) 2013-09-25 2018-09-11 3M Innovative Properties Company Multi-layered polishing pads
WO2015050690A1 (en) 2013-10-03 2015-04-09 Exxonmobil Research And Engineering Company Compositions with improved varnish control properties
US9909079B2 (en) 2013-10-18 2018-03-06 Chevron Oronite Company Llc Lubricating oil composition for protection of silver bearings in medium speed diesel engines
US9062271B2 (en) 2013-10-30 2015-06-23 Chevron Oronite Technology B.V. Process for preparing an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition
US10364403B2 (en) 2013-11-06 2019-07-30 Chevron Oronite Technology B.V. Marine diesel cylinder lubricant oil compositions
US10669506B2 (en) 2013-11-06 2020-06-02 Chevron Oronite Technology B.V. Marine diesel cylinder lubricant oil compositions
WO2015088893A1 (en) 2013-12-10 2015-06-18 The Lubrizol Corporation Organic salts of glyceride-cyclic carboxylic acid anhydride adducts as corrosion inhibitors
US9688605B2 (en) 2013-12-10 2017-06-27 The Lubrizol Corporation Organic salts of glyceride-cyclic carboxylic acid anhydride adducts as corrosion inhibitors
WO2015095336A1 (en) 2013-12-18 2015-06-25 Chevron Phillips Chemical Company Lp Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins
US9708549B2 (en) 2013-12-18 2017-07-18 Chevron Phillips Chemical Company Lp Method for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins
US10208269B2 (en) 2013-12-23 2019-02-19 Exxonmobil Research And Engineering Company Low viscosity ester lubricant and method for using
WO2015099820A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9506008B2 (en) 2013-12-23 2016-11-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US10190072B2 (en) 2013-12-23 2019-01-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9885004B2 (en) 2013-12-23 2018-02-06 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099819A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099907A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Low viscosity ester lubricant and method for using
WO2015099821A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US11168273B2 (en) 2014-01-29 2021-11-09 Basf Se Polycarboxylic acid-based additives for fuels and lubricants
WO2015113681A1 (en) 2014-01-29 2015-08-06 Basf Se Polycarboxylic-acid-based additives for fuels and lubricants
EP3363879A2 (en) 2014-01-29 2018-08-22 Basf Se Diesel fuels, containing polycarboxylic acid-based additives
US11634654B2 (en) 2014-01-29 2023-04-25 Basf Se Polycarboxylic acid-based additives for fuels and lubricants
WO2015157071A1 (en) 2014-04-08 2015-10-15 Lubrizol Advanced Materials, Inc. Ink jet ink compositions
EP2940110A1 (en) 2014-04-29 2015-11-04 Infineum International Limited Lubricating oil compositions
EP3415589A1 (en) 2014-04-29 2018-12-19 Infineum International Limited Lubricating oil compositions
WO2015171292A1 (en) 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
US9896634B2 (en) 2014-05-08 2018-02-20 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
WO2015171978A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171981A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
US10519394B2 (en) 2014-05-09 2019-12-31 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness
WO2015171980A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015183455A1 (en) 2014-05-29 2015-12-03 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US9506009B2 (en) 2014-05-29 2016-11-29 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2015200592A1 (en) 2014-06-27 2015-12-30 The Lubrizol Corporation Mixtures of friction modifiers to provide good friction performance to transmission fluids
US10689593B2 (en) 2014-08-15 2020-06-23 Exxonmobil Research And Engineering Company Low viscosity lubricating oil compositions for turbomachines
US10450525B2 (en) 2014-08-27 2019-10-22 Chevron Oronite Company Llc Process for alaknolamide synthesis
WO2016043944A1 (en) 2014-09-17 2016-03-24 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9944877B2 (en) 2014-09-17 2018-04-17 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9957459B2 (en) 2014-11-03 2018-05-01 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2016073149A1 (en) 2014-11-03 2016-05-12 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
US10920161B2 (en) 2014-11-03 2021-02-16 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2016077134A1 (en) 2014-11-12 2016-05-19 The Lubrizol Corporation Mixed phosphorus esters for lubricant applications
EP3020790A1 (en) 2014-11-14 2016-05-18 Chevron Oronite Technology B.V. Trunk piston engine oil composition for low sulfur marine distillate fueled engines
US9506007B2 (en) 2014-11-14 2016-11-29 Chevron Oronite Technology B.V. Low sulfur marine distillate fuel trunk piston engine oil composition
EP4089158A1 (en) 2014-11-14 2022-11-16 Chevron Oronite Technology B.V. Low sulfur marine distillate fuel trunk piston engine oil composition
US9879202B2 (en) 2014-12-04 2018-01-30 Infineum International Limited Marine engine lubrication
EP3029133A1 (en) 2014-12-04 2016-06-08 Infineum International Limited Marine engine lubrication
US10364404B2 (en) 2014-12-04 2019-07-30 Infineum International Limited Marine engine lubrication
WO2016106211A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for authentication and identification of petroleum products
WO2016106214A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for determining condition and quality of petroleum products
US10000721B2 (en) 2014-12-30 2018-06-19 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US10781397B2 (en) 2014-12-30 2020-09-22 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US10000717B2 (en) 2014-12-30 2018-06-19 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109322A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109325A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109376A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US10066184B2 (en) 2014-12-30 2018-09-04 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109382A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US9926509B2 (en) 2015-01-19 2018-03-27 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection and solubility
US9528074B2 (en) 2015-02-13 2016-12-27 Chevron Oronite Technology B.V. Lubricating oil compositions with enhanced piston cleanliness
US9528071B2 (en) 2015-02-13 2016-12-27 Chevron Oronite Technology B.V. Lubricating oil compositions with enhanced piston cleanliness
US10150930B2 (en) 2015-02-18 2018-12-11 Chevron Oronite Technology B.V. Low sulfur marine distillate fuel trunk piston engine oil composition
US10138438B2 (en) 2015-02-18 2018-11-27 Chevron Oronite Technology B.V. Low sulfur marine distillate fuel trunk piston engine oil composition
WO2016144639A1 (en) 2015-03-10 2016-09-15 The Lubrizol Corporation Lubricating compositions comprising an anti-wear/friction modifying agent
US10556316B2 (en) 2015-05-13 2020-02-11 3M Innovative Properties Company Polishing pads and systems for and methods of using same
WO2016191409A1 (en) 2015-05-28 2016-12-01 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US10119093B2 (en) 2015-05-28 2018-11-06 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016200606A1 (en) 2015-06-09 2016-12-15 Exxonmobil Research And Engineering Company Inverse micellar compositions containing lubricant additives
US10119090B2 (en) 2015-07-07 2018-11-06 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2017007670A1 (en) 2015-07-07 2017-01-12 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9732300B2 (en) 2015-07-23 2017-08-15 Chevron Phillipa Chemical Company LP Liquid propylene oligomers and methods of making same
US10689589B2 (en) 2015-07-28 2020-06-23 Innospec Limited Cyclic quaternary ammonium salts as fuel or lubricant additives
US10435491B2 (en) 2015-08-19 2019-10-08 Chevron Phillips Chemical Company Lp Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins
EP3135750A1 (en) 2015-08-26 2017-03-01 Infineum International Limited Lubricating oil compositions
WO2017083042A1 (en) 2015-11-09 2017-05-18 The Lubrizol Corporation Using quaternary amine additives to improve water separation
US10316712B2 (en) 2015-12-18 2019-06-11 Exxonmobil Research And Engineering Company Lubricant compositions for surface finishing of materials
US10550341B2 (en) 2015-12-28 2020-02-04 Exxonmobil Research And Engineering Company Sequential deasphalting for base stock production
US10590360B2 (en) 2015-12-28 2020-03-17 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
US10947464B2 (en) 2015-12-28 2021-03-16 Exxonmobil Research And Engineering Company Integrated resid deasphalting and gasification
US10550335B2 (en) 2015-12-28 2020-02-04 Exxonmobil Research And Engineering Company Fluxed deasphalter rock fuel oil blend component oils
US10647925B2 (en) 2015-12-28 2020-05-12 Exxonmobil Research And Engineering Company Fuel components from hydroprocessed deasphalted oils
US10808185B2 (en) 2015-12-28 2020-10-20 Exxonmobil Research And Engineering Company Bright stock production from low severity resid deasphalting
WO2017117178A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
WO2017142805A1 (en) 2016-02-16 2017-08-24 3M Innovative Properties Company Polishing systems and methods of making and using same
WO2017146897A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
US10377961B2 (en) 2016-02-26 2019-08-13 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
US10377962B2 (en) 2016-02-26 2019-08-13 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017146896A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017172254A1 (en) 2016-03-31 2017-10-05 Exxonmobil Research And Engineering Company Lubricant compositions
US9951290B2 (en) 2016-03-31 2018-04-24 Exxonmobil Research And Engineering Company Lubricant compositions
US10494579B2 (en) 2016-04-26 2019-12-03 Exxonmobil Research And Engineering Company Naphthene-containing distillate stream compositions and uses thereof
US10494583B2 (en) 2016-05-17 2019-12-03 Afton Chemical Corporation Synergistic dispersants
US10179886B2 (en) 2016-05-17 2019-01-15 Afton Chemical Corporation Synergistic dispersants
EP3246383A1 (en) 2016-05-17 2017-11-22 Afton Chemical Corporation Synergistic dispersants
WO2017200688A1 (en) 2016-05-18 2017-11-23 The Lubrizol Corporation Hydraulic fluid composition
US11261398B2 (en) 2016-05-18 2022-03-01 The Lubrizol Corporation Hydraulic fluid composition
WO2017205274A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205270A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017205271A1 (en) 2016-05-24 2017-11-30 The Lubrizol Corporation Seal swell agents for lubricating compositions
WO2017218664A1 (en) 2016-06-17 2017-12-21 The Lubrizol Corporation Lubricating compositions
US11078418B2 (en) 2016-07-05 2021-08-03 Basf Se Corrosion inhibitors for fuels and lubricants
WO2018013249A1 (en) 2016-07-12 2018-01-18 Chevron Phillips Chemical Company Lp Decene oligomers
US10647626B2 (en) 2016-07-12 2020-05-12 Chevron Phillips Chemical Company Lp Decene oligomers
US10174272B2 (en) 2016-07-14 2019-01-08 Afton Chemical Corporation Dispersant viscosity index improver-containing lubricant compositions and methods of use thereof
WO2018017449A1 (en) 2016-07-20 2018-01-25 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants
WO2018017454A1 (en) 2016-07-20 2018-01-25 The Lubrizol Corporation Alkyl phosphate amine salts for use in lubricants
WO2018026982A1 (en) 2016-08-03 2018-02-08 Exxonmobil Research And Engineering Company Lubricating engine oil for improved wear protection and fuel efficiency
WO2018027227A1 (en) 2016-08-05 2018-02-08 Rutgers, The State University Of New Jersey Thermocleavable friction modifiers and methods thereof
US10640725B2 (en) 2016-08-05 2020-05-05 Rutgers, The State University Of New Jersey Thermocleavable friction modifiers and methods thereof
WO2018057377A1 (en) 2016-09-20 2018-03-29 Exxonmobil Research And Engineering Company Non-newtonian engine oil with superior engine wear protection and fuel economy
US10479956B2 (en) 2016-09-20 2019-11-19 Exxonmobil Research And Engineering Company Non-newtonian engine oil with superior engine wear protection and fuel economy
WO2018057675A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Polyacrylate antifoam components with improved thermal stability
WO2018057678A1 (en) 2016-09-21 2018-03-29 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
WO2018067905A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains
WO2018067906A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company High conductivity lubricating oils for electric and hybrid vehicles
WO2018067903A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains
WO2018067902A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Lubricating oil compositions for electric vehicle powertrains
WO2018067908A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Low conductivity lubricating oils for electric and hybrid vehicles
WO2019117992A1 (en) 2016-12-13 2019-06-20 Afton Chemical Corporation Polyolefin-derived dispersants
US10584297B2 (en) 2016-12-13 2020-03-10 Afton Chemical Corporation Polyolefin-derived dispersants
EP3336163A1 (en) 2016-12-13 2018-06-20 Afton Chemical Corporation Polyolefin-derived dispersants
WO2018111846A1 (en) 2016-12-13 2018-06-21 Afton Chemical Corporation Polyolefin-derived dispersants
WO2018118477A1 (en) 2016-12-19 2018-06-28 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition compression spark ignition engines
US10829708B2 (en) 2016-12-19 2020-11-10 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2018118163A1 (en) 2016-12-22 2018-06-28 The Lubrizol Corporation Fluorinated polyacrylate antifoam components for lubricating compositions
US10647936B2 (en) 2016-12-30 2020-05-12 Exxonmobil Research And Engineering Company Method for improving lubricant antifoaming performance and filterability
WO2018125956A1 (en) 2016-12-30 2018-07-05 Exxonmobil Research And Engineering Company Low viscosity lubricating oil compositions for turbomachines
WO2018144167A1 (en) 2017-02-01 2018-08-09 Exxonmobil Research And Engineering Company Lubricating engine oil and method for improving engine fuel efficiency
WO2018144166A1 (en) 2017-02-01 2018-08-09 Exxonmobil Research And Engineering Company Lubricating engine oil and method for improving engine fuel efficiency
US10793801B2 (en) 2017-02-06 2020-10-06 Exxonmobil Chemical Patents Inc. Low transition temperature mixtures and lubricating oils containing the same
US10487289B2 (en) 2017-02-21 2019-11-26 Exxonmobil Research And Engineering Company Lubricating oil compositions and methods of use thereof
WO2018156304A1 (en) 2017-02-21 2018-08-30 Exxonmobil Research And Engineering Company Lubricating oil compositions and methods of use thereof
EP3369802A1 (en) 2017-03-01 2018-09-05 Infineum International Limited Improvements in and relating to lubricating compositions
US10240102B2 (en) 2017-03-16 2019-03-26 Chevron Phillips Chemical Company, Lp Lubricant compositions containing hexene-based oligomers
WO2018170110A1 (en) 2017-03-16 2018-09-20 Chevron Phillips Chemical Company Lp Lubricant compositions containing hexene-based oligomers
US10876062B2 (en) 2017-03-24 2020-12-29 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
US10858610B2 (en) 2017-03-24 2020-12-08 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
WO2018175830A1 (en) 2017-03-24 2018-09-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency and energy efficiency
US10738258B2 (en) 2017-03-24 2020-08-11 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency and energy efficiency
US10808196B2 (en) 2017-03-28 2020-10-20 Exxonmobil Chemical Patents Inc. Cold cranking simulator viscosity reducing base stocks and lubricating oil formulations containing the same
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use
WO2018197312A1 (en) 2017-04-27 2018-11-01 Shell Internationale Research Maatschappij B.V. Lubricating composition
WO2018236592A1 (en) 2017-06-20 2018-12-27 The Lubrizol Corporation Lubricating composition
EP3421576A1 (en) 2017-06-30 2019-01-02 Infineum International Limited Refinery antifoulant process
WO2019014092A1 (en) 2017-07-13 2019-01-17 Exxonmobil Research And Engineering Company Continuous process for the manufacture of grease
WO2019018145A1 (en) 2017-07-21 2019-01-24 Exxonmobil Research And Engineering Company Method for improving deposit control and cleanliness performance in an engine lubricated with a lubricating oil
WO2019028310A1 (en) 2017-08-04 2019-02-07 Exxonmobil Research And Engineering Company Novel formulation for lubrication of hyper compressors providing improved pumpability under high-pressure conditions
WO2019055291A1 (en) 2017-09-18 2019-03-21 Exxonmobil Research And Engineering Company Hydraulic oil compositions with improved hydrolytic and thermo-oxidative stability
WO2019060144A1 (en) 2017-09-22 2019-03-28 Exxonmobil Research And Engineering Company Lubricating oil compositions with viscosity and deposit control
EP3461877A1 (en) 2017-09-27 2019-04-03 Infineum International Limited Improvements in and relating to lubricating compositions
WO2019089181A1 (en) 2017-10-30 2019-05-09 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2019089180A1 (en) 2017-10-30 2019-05-09 Exxonmobil Research And Engineering Company Lubricating oil compositions having improved cleanliness and wear performance
US10738262B2 (en) 2017-10-30 2020-08-11 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2019089177A1 (en) 2017-10-30 2019-05-09 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2019090038A1 (en) 2017-11-03 2019-05-09 Exxonmobil Research And Engineering Company Lubricant compositions with improved performance and methods of preparing and using the same
WO2019094019A1 (en) 2017-11-09 2019-05-16 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness
WO2019103808A1 (en) 2017-11-22 2019-05-31 Exxonmobil Research And Engineering Company Lubricating oil compositions with oxidative stability in diesel engines
WO2019112711A1 (en) 2017-12-04 2019-06-13 Exxonmobil Research And Enginerring Company Method for preventing or reducing low speed pre-ignition
EP3495462A1 (en) 2017-12-11 2019-06-12 Infineum International Limited Low ash and ash-free acid neutralizing compositions and lubricating oil compositions containing same
US10731103B2 (en) 2017-12-11 2020-08-04 Infineum International Limited Low ash and ash-free acid neutralizing compositions and lubricating oil compositions containing same
WO2019118115A1 (en) 2017-12-15 2019-06-20 Exxonmobil Research And Engineering Company Lubricating oil compositions containing microencapsulated additives
WO2019133411A1 (en) 2017-12-28 2019-07-04 Exxonmobil Research And Engineering Company Flat viscosity fluids and lubricating oils based on liquid crystal base stocks
WO2019133407A1 (en) 2017-12-28 2019-07-04 Exxonmobil Research And Engineering Company Low traction/energy efficient liquid crystal base stocks
WO2019133409A1 (en) 2017-12-28 2019-07-04 Exxonmobil Research And Engineering Company Friction and wear reduction using liquid crystal base stocks
WO2019133191A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Lubrication of oxygenated diamond-like carbon surfaces
US10774286B2 (en) 2017-12-29 2020-09-15 Exxonmobil Research And Engineering Company Grease compositions with improved performance and methods of preparing and using the same
WO2019133255A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Grease compositions with improved performance comprising thixotropic polyamide, and methods of preparing and using the same
WO2019133218A1 (en) 2017-12-29 2019-07-04 Exxonmobil Research And Engineering Company Lubricating oil compositions with wear and sludge control
WO2019183365A1 (en) 2018-03-21 2019-09-26 The Lubrizol Corporation NOVEL FLUORINATED POLYACRYLATES ANTIFOAMS IN ULTRA-LOW VISCOSITY (<5 CST) finished fluids
EP4079828A1 (en) 2018-03-29 2022-10-26 Innospec Limited Composition, method and use
WO2019217058A1 (en) 2018-05-11 2019-11-14 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2019240965A1 (en) 2018-06-11 2019-12-19 Exxonmobil Research And Engineering Company Non-zinc-based antiwear compositions, hydraulic oil compositions, and methods of using the same
EP3597726A1 (en) 2018-07-20 2020-01-22 Afton Chemical Corporation Fuel-soluble synergistic cleaning mixture for high pressure gasoline engines
WO2020023430A1 (en) 2018-07-23 2020-01-30 Exxonmobil Research And Engineering Company Lubricating oil compositions with oxidative stability in diesel engines using biodiesel fuel
WO2020023437A1 (en) 2018-07-24 2020-01-30 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine corrosion protection
US10774722B2 (en) 2018-09-04 2020-09-15 Afton Chemical Corporation Predictive methods for emissions control systems performance
US11401855B2 (en) 2018-09-04 2022-08-02 Afton Chemical Corporation Predictive methods for emissions control systems performance
US11441458B2 (en) 2018-09-04 2022-09-13 Afton Chemical Corporation Gasoline particulate filters with high initial filtering efficiency and methods of making same
US10774708B2 (en) 2018-09-04 2020-09-15 Afton Chemical Corporation Gasoline particulate filters with high initial filtering efficiency and methods of making same
WO2020068439A1 (en) 2018-09-27 2020-04-02 Exxonmobil Research And Engineering Company Low viscosity lubricating oils with improved oxidative stability and traction performance
WO2020096804A1 (en) 2018-11-05 2020-05-14 Exxonmobil Research And Engineering Company Lubricating oil compositions having improved cleanliness and wear performance
WO2020112338A1 (en) 2018-11-28 2020-06-04 Exxonmobil Research And Engineering Company Lubricating oil compositions with improved deposit resistance and methods thereof
WO2020123440A1 (en) 2018-12-10 2020-06-18 Exxonmobil Research And Engineering Company Method for improving oxidation and deposit resistance of lubricating oils
WO2020132166A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricating oil compositions with antioxidant formation and dissipation control
WO2020131310A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Method for improving high temperature antifoaming performance of a lubricating oil
WO2020131440A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having calcium sulfonate and polyurea thickeners
WO2020131515A2 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricant compositions with improved wear control
WO2020131441A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having improved performance
WO2020132164A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Lubricating oil compositions with viscosity control
WO2020131439A1 (en) 2018-12-19 2020-06-25 Exxonmobil Research And Engineering Company Grease compositions having polyurea thickeners made with isocyanate terminated prepolymers
EP3835392A1 (en) 2018-12-20 2021-06-16 Infineum International Limited Hydrocarbon marine fuel oil
EP3760696A1 (en) 2018-12-20 2021-01-06 Infineum International Limited Oil anti-foulant and/or asphaltene agglomeration process
WO2020139333A1 (en) 2018-12-26 2020-07-02 Exxonmobil Research And Engineering Company Formulation approach to extend the high temperature performance of lithium complex greases
EP3680312A1 (en) 2019-01-11 2020-07-15 Afton Chemical Corporation Oxazoline modified dispersants
WO2020150123A1 (en) 2019-01-17 2020-07-23 The Lubrizol Corporation Traction fluids
WO2020149958A1 (en) 2019-01-18 2020-07-23 Afton Chemical Corporation Engine oils for soot handling and friction reduction
US11008527B2 (en) 2019-01-18 2021-05-18 Afton Chemical Corporation Engine oils for soot handling and friction reduction
EP3690009A1 (en) 2019-01-31 2020-08-05 Afton Chemical Corporation Fuel additive mixture providing rapid injector clean-up in high pressure gasoline engines
WO2020176171A1 (en) 2019-02-28 2020-09-03 Exxonmobil Research And Engineering Company Low viscosity gear oil compositions for electric and hybrid vehicles
US11396639B2 (en) 2019-05-13 2022-07-26 Afton Chemical Corporation Additive and lubricant for industrial lubrication
EP3739025A1 (en) 2019-05-13 2020-11-18 Afton Chemical Corporation Additive and lubricant for industrial lubrication
WO2020257370A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257377A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257373A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257368A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
US11092393B1 (en) 2019-06-19 2021-08-17 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257374A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
US10712105B1 (en) 2019-06-19 2020-07-14 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257378A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257371A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257379A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257376A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020257375A1 (en) 2019-06-19 2020-12-24 Exxonmobil Research And Engineering Company Heat transfer fluids and methods of use
WO2020264534A2 (en) 2019-06-27 2020-12-30 Exxonmobil Research And Engineering Company Method for reducing solubilized copper levels in wind turbine gear oils
EP3778841A1 (en) 2019-08-15 2021-02-17 Infineum International Limited Method for reducing piston deposits in a marine diesel engine
WO2021090021A1 (en) 2019-11-08 2021-05-14 Innospec Limited Compositions, and methods and uses relating thereto
WO2021090020A1 (en) 2019-11-08 2021-05-14 Innospec Limited Compositions and methods and uses relating thereto
EP3825387A1 (en) 2019-11-22 2021-05-26 Afton Chemical Corporation Fuel-soluble cavitation inhibitor for fuels used in common-rail injection engines
WO2021138285A1 (en) 2020-01-03 2021-07-08 Afton Chemical Corporation Silicone functionlized viscosity index improver
US11214753B2 (en) 2020-01-03 2022-01-04 Afton Chemical Corporation Silicone functionalized viscosity index improver
WO2021154497A1 (en) 2020-01-30 2021-08-05 Exxonmobil Research And Engineering Company Sulfur-free, ashless, low phosphorus lubricant compositions with improved oxidation stability
WO2021183230A1 (en) 2020-03-12 2021-09-16 The Lubrizol Corporation Oil-based corrosion inhibitors
WO2021194813A1 (en) 2020-03-27 2021-09-30 Exxonmobil Research And Engineering Company Monitoring health of heat transfer fluids for electric systems
WO2022009105A1 (en) 2020-07-07 2022-01-13 Chevron Oronite Company Llc Fuel additives for mitigating injector nozzle fouling and reducing particulate emissions
WO2022010606A1 (en) 2020-07-09 2022-01-13 Exxonmobil Research And Engineering Company Engine oil lubricant compositions and methods for making same with superior engine wear protection and corrosion protection
WO2022058894A1 (en) 2020-09-17 2022-03-24 Chevron Oronite Company Llc Aryloxy alkylamines as fuel additives for reducing injector fouling in direct injection spark ignition gasoline engines
WO2022072962A1 (en) 2020-09-30 2022-04-07 Exxonmobil Research And Engineering Company Low friction and low traction lubricant compositions useful in dry clutch motorcycles
WO2022099291A1 (en) 2020-11-06 2022-05-12 Exxonmobil Research And Engineering Company Engine oil lubricant compositions and methods for making same with steel corrosion protection
US11760952B2 (en) 2021-01-12 2023-09-19 Ingevity South Carolina, Llc Lubricant thickener systems from modified tall oil fatty acids, lubricating compositions, and associated methods
WO2022263254A1 (en) 2021-06-15 2022-12-22 Basf Se New gasoline additive packages
EP4105301A1 (en) 2021-06-15 2022-12-21 Basf Se New gasoline additive packages
WO2023057943A1 (en) 2021-10-06 2023-04-13 Chevron Oronite Company Llc Fuel additives for lowering deposit and particulate emission
US12031099B2 (en) 2021-11-15 2024-07-09 Infineum International Limited Marine fuels
EP4180505A1 (en) 2021-11-15 2023-05-17 Infineum International Limited Improvements in marine fuels
WO2023111550A1 (en) 2021-12-14 2023-06-22 Innospec Limited Methods and uses relating to fuel compositions
WO2023122405A1 (en) 2021-12-21 2023-06-29 ExxonMobil Technology and Engineering Company Engine oil lubricant compostions and methods for making same with superior oil consumption
EP4212604A1 (en) 2022-01-13 2023-07-19 TotalEnergies One Tech Stabilised compositions comprising olefins
WO2023134977A1 (en) 2022-01-13 2023-07-20 Totalenergies Onetech Processing of stabilised compositions comprising olefins
EP4282937A1 (en) 2022-05-26 2023-11-29 Afton Chemical Corporation Engine oil formluation for controlling particulate emissions
EP4296338A1 (en) 2022-06-20 2023-12-27 Afton Chemical Corporation Phosphorus antiwear system for improved gear protection
US11639480B1 (en) 2022-06-20 2023-05-02 Afton Chemical Corporation Phosphorus antiwear system for improved gear protection
WO2023247973A1 (en) 2022-06-24 2023-12-28 Innospec Limited Fuel compositions comprising an additive, and methods and uses relating thereto
WO2024006132A1 (en) 2022-06-27 2024-01-04 The Lubrizol Corporation Lubricating composition
EP4342964A1 (en) 2022-09-22 2024-03-27 Afton Chemical Corporation Extreme pressure additives with improved copper corrosion
EP4353805A1 (en) 2022-10-11 2024-04-17 Infineum International Limited Lubricant composition containing metal alkanoate
EP4353804A1 (en) 2022-10-11 2024-04-17 Infineum International Limited Functionalized c4 to c5 olefin polymers and lubricant compositions containing such
EP4357443A1 (en) 2022-10-18 2024-04-24 Infineum International Limited Lubricating oil compositions
WO2024086192A1 (en) 2022-10-18 2024-04-25 The Lubrizol Corporation Hydraulic fluid composition
EP4368687A1 (en) 2022-11-10 2024-05-15 Afton Chemical Corporation Corrosion inhibitor and industrial lubricant including the same
EP4386070A1 (en) 2022-12-09 2024-06-19 Afton Chemical Corporation Driveline and transmission fluids for low speed wear and scuffing
WO2024126998A1 (en) 2022-12-12 2024-06-20 Innospec Limited Composition, method and use
EP4397738A1 (en) 2023-01-03 2024-07-10 Infineum International Limited Method for reduction of abnormal combustion events
EP4442797A1 (en) 2023-03-03 2024-10-09 Afton Chemical Corporation Lubricating composition for gear fluids
EP4428212A1 (en) 2023-03-10 2024-09-11 Infineum International Limited Asphaltene deposition control
WO2024206634A1 (en) 2023-03-29 2024-10-03 Chevron Oronite Company Llc Fuel additive compositions and methods for controlling carbon deposits in an internal combustion engines
US11884892B1 (en) 2023-03-31 2024-01-30 Afton Chemical Corporation Antiwear system for improved copper corrosion
US11958875B1 (en) 2023-03-31 2024-04-16 Afton Chemical Corporation Thiophosphoric acid products for antiwear additives
US12054688B1 (en) 2023-03-31 2024-08-06 Afton Chemical Corporation Antiwear system for improved copper corrosion
EP4438611A1 (en) 2023-03-31 2024-10-02 Afton Chemical Corporation Thiophosphoric acid products for antiwear additives
EP4438699A1 (en) 2023-03-31 2024-10-02 Afton Chemical Corporation Antiwear system for improved copper corrosion
EP4438701A1 (en) 2023-03-31 2024-10-02 Afton Chemical Corporation Antiwear system for improved copper corrosion
EP4438700A1 (en) 2023-03-31 2024-10-02 Afton Chemical Corporation Antiwear system for improved copper corrosion
US11884893B1 (en) 2023-03-31 2024-01-30 Afton Chemical Corporation Antiwear system for improved copper corrosion

Also Published As

Publication number Publication date
DE1545487A1 (en) 1970-07-02
DE1289355B (en) 1975-06-12
DE1545487B2 (en) 1980-02-14
FR1492000A (en) 1967-08-11
DE1545487C3 (en) 1980-10-16
GB1094020A (en) 1967-12-06
JPS4945685B1 (en) 1974-12-05
FR1489559A (en) 1967-07-21
US3574576A (en) 1971-04-13
MY7000109A (en) 1970-12-31
DE1289355C2 (en) 1975-06-12
US3438757A (en) 1969-04-15
BE744693Q (en) 1970-07-01
GB1083610A (en) 1967-09-20

Similar Documents

Publication Publication Date Title
US3565804A (en) Lubricating oil additives
US3131150A (en) Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3154560A (en) Nu, nu&#39;-azaalkylene-bis
US3275554A (en) Polyolefin substituted polyamines and lubricants containing them
US3844958A (en) Hydrocarbyl amines for lubricating oil detergents
US3749695A (en) Lubricating oil additives
US3361673A (en) Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine
US3024195A (en) Lubricating oil compositions of alkylpiperazine alkenyl succinimides
US3018250A (en) Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides
US3340281A (en) Method for producing lubricating oil additives
US3455827A (en) Maleic anhydride copolymer succinimides of long chain hydrocarbon amines
US3443918A (en) Gasoline composition
US3785980A (en) Reaction product of an amine and a hydroperoxidized ethylene/propylene copolymer
US3018247A (en) Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends
US3235503A (en) Lubricant containing alkylene polyamine reaction product
US3189544A (en) Non-ash-containing lubricating oil composition
US3184411A (en) Lubricants for reducing corrosion
US3898056A (en) Hydrocarbylamine additives for distillate fuels
US3864098A (en) Fuel additives
US3525693A (en) Alkenyl succinic polyglycol ether
GB1577590A (en) Lubricating oil composition
US3287271A (en) Combined detergent-corrosion inhibitors
CA1038851A (en) Dispersant-detergent libricant and fuel additives
US3432479A (en) Reaction product of monoamine,polyamine and polymer of a monovinyl monomer and maleic anhydride
US3873460A (en) Lubricating oil composition containing polyamine dispersants